International Union of Pure and Applied Chemistry

Division VIII Chemical Nomenclature and Structure Representation Division Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013.

Prepared for publication by Henri A. Favre and Warren H. Powell, Royal Society of Chemistry, ISBN 978-0-85404-182-4

Appendix 3. STRUCTURES FOR ALKALOIDS, STEROIDS, TERPENOIDS, AND SIMILAR COMPOUNDS

1. Alkaloids

H 13 12 16 17 H 14 1 H 2 10 9 11 15 HN20 8 3 5 4 H 7 H 6 19 H aconitane

16

17 H 5 9 6 21 19 18 8 N CH2-CH3 10 7 H 4 2 20 1 3 11 H 13 N H 14 15 12 CH3 22 ajmalan

17 CH3 16 6 5 H 21 9 4 H 8 N 10 7 2 20 19 1 3 CH 11 3 13 N H 14 15 18 12 akuammilan (named systematically by CAS)

24 17 H O 5 21 16 6 4 15 20 9 N 7 H3C 10 8 23 H CH2-CH3 14 19 18 1 2 3 11 13 N 12 CH3 22 alstophyllan (named systematically by CAS) 3 4 2 5

6 1 N 11b 6a CH3 H 12 11a 11 7

10 8 9 aporphine (named systematically by CAS)

8 7 9 N H 6 10 19 5 14 11 21 4 15 20 13 12 3 1 2 16 18 N 17 H aspidofractinine (named systematically by CAS)

8 7 9 6 N 10 19 CH2-CH3 5 20 21 14 11 H 4 15 13 12 2 3 1 16 18 N H 17 H aspidospermidine

17 12 CH 16 3 11 20 14 H 13 1 9 15 2 10 8 HN21 H 5 3 4 7 6 19 H CH3 18 atidane (named systematically by CAS)

17 24 12 16 CH2 23 O 11 20 14 13 22 1 9 H 2 15 10 8 OH N21 H 5 3 4 7 H 6 19 CH3 18 atisine (named systematically by CAS) 4 5 5’ 4’ 3 6 6’ 3’ 2 2 7’ ’ HN 1 7 1’ NH H 8 O 8’ H 10 14 15 ’ 11 13’ 15’ 9 9 O ’ 14 12 12’ 10’ 13 11’ berbaman (named systematically by CAS)

4 5 4a 3 6

7 2 13a N 13b 8 1 H 8a 13 9 12a

12 10 11 berbine (named systematically by CAS)

O-CH3 21 HO 2 H 3 1 6 18 14 4 7 O 15 13 5 19 H N 8 9 O 16 12 10 20 17 11 cephalotaxine

27 H CH3 24 25 26 H 23

28 N 22 H 18 H 20 13 H CH3 17 21 11 12 19 H 16 1 CH3 H 14 9 2 15 10 8 H H 5 3 7 4 6 H cevane

16 O17

15 O 3 25 4 2 CH3 H 1 N 18 5 6 24 14 13 19 20 12 11 23 7 O H 21 HO H 10 8 O 9 22 chelidonine (named systematically by CAS) 10 11 4 CH=CH2 3 7 H 5 H 8 2 9 1N 5’ 4 10’ ’ 6 6’ 3’

7 2’ ’ 9’ N 8’ 1’ cinchonan

23 CH3 21 CH3 22N 18 20 H 12 H 11 17 19 13 CH3 H 16 1 9 14 2 10 8 15 H H 7 3 5 4 6 conanine

6 5 4 21 9 7 19 18 8 N 10 CH-CH3 3 20 H 1 2 15 11 13 N H 14 H 12 H CH-CH3 16 17 corynan (named systematically by CAS)

19 18 21 5 4 CH-CH3 N 20 H 6 H 15 9 7 8 H 10 3 CH-CH 2 3 1 16 17 11 13 N 12 H corynoxan (named systematically by CAS)

2 1 3 11 17 10 19 O 9 18 4 13 12 16 H N O 8 14 5 15 7 6 crinan (named systematically by CAS)

19 18 21 CH CH 4 20 2 3 N 5 3 14 H 9 6 7 H 15 H 10 8 2 16 H 11 13 NH H CH3 12 1 17 curan 21 22 23 19 CH2-CH2-CH3 CH3 H H H 7 9 CH 8 H C 17 10 3 3 2 1 12 18 4 N 11 5 16 13

6 15 14 CH3 20 daphnane (named systematically by CAS)

H 2 3 4 18 14 CH3 H3C N 1 11 5 10 6 O 12 H 13 H 8 H 9 7 H 15 16 H HC CH3

CH3 17 dendrobane (named systematically by CAS)

10 9 6 8 11 7 5

H 4 12 13 N 2 19 1 N 3 16 14 17 18 15 CH2-CH3 20 21 eburnamenine

9 7 8 10 6

5 11 N 13 4 12 14 H 16 17 3 1 CH2-CH3 2 H H 15 H 8’ 1 9’ HN ’ 7’ 2’

3’ 6’ 10’ 4’ 5’ emetan (named systematically by CAS)

7 8 6 NH H 9 10 5 4 H 11 3 16 12 2 1 13 15 N 14 H ergoline H 17 5’ 7 3 19 18 6 CH3 4’ ’ 6’ N NH CH2 8 N H H 2’ 7’ 12’ 9 N H 5 O 10 4 8’ 11’ 1’ H 11 3 16 9 10 12 ’ ’ 2 1 13 N 15 H 14 ergotaman

2 3 1 H 6 7 14 4 5 15 N 8 13 9 16 12 10 17 11 erythrinan

15 CH2-O-Ac O-Ac Ac-O H H O Ac-O 9 1 6 8 H 2 10 7 3 5 O-Ac H 4 O CH3 28 O 11 13 HO CH3 29 14 12 30 27 O H3C 26 O O H 16 25 24 17 23 18

22 N 19

21 20 evonimine (named systematically by CAS)

15 CH2-O-Ac O-Ac Ac-O H H O Ac-O 9 1 6 8 H 2 10 7 3 5 O-Ac H 4 O CH3 27O 11 13 HO CH3 28 29 14 12 26 CH O 3 O 25 H O 16 17 H 24 23 18 CH3 30 22 N 19

21 20 evonine (named systematically by CAS) H 5 21 19 4 N 20 O 18 6 9 H 15 7 17 8 3 10 16 14 H 2 11 1 13 N 12 H formosanan (named systematically by CAS)

H OH H 4 5 3 O 2 13 1 CH3-O 6 12a 12 12b 11 7 10 N 8 9 CH3 14 galanthamine (named systematically by CAS)

2 1 3 H 11 15 12 14 10 16 H H 4 9 N 13 6 5 8 7 galanthan (named systematically by CAS)

2 3 1

11 4 10 12 15 16 13 9 5 14 NH 17 6 8 7 hasubanan

13 H 17 12 CH 11 2 20 14 16 1 9 15 2 21 N 10 8 H 5 3 4 7 H 6 19 CH3 18 hetisan

7 6 8 20 21 N 19 11 CH2-CH3 10 9 H 5 12 4 H H 16 17 18 3 13 15 N 14 H 1 2 ibogamine 8 7 9 N H 6 10 5 19 14 22 20 11 4 15 12 3 13 2 1 21 16 18 N 17 H kopsan (named systematically by CAS)

20 18 19 HN 17 21 22 HN 16 O 23 15 24 14 HN 25 13 5 4 26 8 O 6 3 28 9 7 O 27 1 2 10 12 O H 11 29 lunarine (named systematically by CAS)

15 8 H 11 7 6 10 12 14 H 5 9 N 13 17 4

1 3 2 lycopodane (named systematically by CAS)

2 3 1 H HN 12 17 4 11 H 15 13 5 10 16 H 9 O 14 6 8 7 lycorenan (named systematically by CAS)

13 14 4’ 12 3 ’ 5’ H O 11

2 6’ ’ 3 2 1 1 ’ H 1’’ 4 10 9 6’’ 2 N ’’ H 5 5’’ 3’’ 6 8 4’’ 7 lythran (named systematically by CAS) 7’’ CH3-O 5’ 6’ 2’’ 3’’

4’ 4’’ 1’ 1’’ 2 3’ ’ 6’’ 5’’ 6 14 OH HO 7 13 8 H H 12 H 9 10 N 11 5 4 H H 1 3 2 lythranidine (named systematically by CAS)

14 15 13 H 16N 17 12 11 H 5 7 8 4 6 H H 3 N 9 1 2 10 matridine (named systematically by CAS)

2 3 1

11 4 10 12 15 16 13 5 9 NH 14 H 17 6 8 7 morphinan

12 H CH3 H 9 2 1 8 10 11 5 7 3 4 N CH3 H O 6 4’ 3’ H

5’ 2’ O 1’ nupharidine (named systematically by CAS) 4 5 3 H 6 7 2 8 N1 17 H H 10 9 H 15 16 11 NH 14 12 NH 18 23 19 13 20 22 21 ormosanine (named systematically by CAS)

10 9 6 11 8 7 5

12 13 1 N 4 N 2 21 H 3 H H 20 14 15 19 H O 16 18 17 18-oxayohimban

4 5 16 3 6

2 5’ 4’ HN 1 7 16’ 17 6’ 8 18’ 3’ H 10 O 15 2 11 ’ NH 7’ 17’ 9 1 8’ ’ H 14 14 ’ 12 O 15’ 13 18 9 13’ ’

12’ 10’ 11’ oxyacanthan (named systematically by CAS)

HO 1 H 15 10 11 11a 2 H O 9 10a 3 OH 4a 13 . 12 4 O 8 6a N H 14 7 6 5 pancracine (named systematically by CAS)

18 17 1 19 16 NH 2 H 5 15 13 14 6 12 3 4 H 7O 9 11 8 10 rheadan (named systematically by CAS) 4 19 20’ 5 O-CH 5’ 4’ 16 6 3 CH3-O 6’ 16’ 3 3’

2 7 2’ 18 N 1 20 1’ N 18’ 17 7 17 H3C O-CH3 ’ ’ CH3 8 8’ H 10 H O19’ 10’ 15 11 11’ 15’ 9 9’

14 21 14 12 ’ O-CH3 HO 12’ 13 13’ rodiasine (named systematically by CAS)

18 12 CH3 17 11 19 13 OH 1 CH3 H 16 2 9 14 H 10 8 15 HN3 O H H 20 5 7 4 4a 6 H samandarine (named systematically by CAS)

17 H 16 CH3 6 5 9 21 H 7 4 N 10 8 20 3 19 1 2 CH 11 3 13 N H 14 15 18 12 H sarpagan

19 H CH3 H 14 13 18 H 12 CH3 15 20 11 16 O10 H3C 17 21 O 9 H H 1 7 8 6 2 N 5 4 3 senecionan (named systematically by CAS)

21 CH H 3 H 18 23 CH3 24 12 20 22 11 17 27 19 16 25 13 N CH3 1 CH3 H H 28 9 14 26 H 2 H 10 8 15 H H 3 7 5 4 6 solanidane (the CAS name requires the chirality at C-22 to be specified) 7 5 H 17 15 16 4 6 N 14 8 11 3 N 13 1 2 12 10 9 H sparteine (named systematically by CAS)

27 21 24 CH3 CH3 H 23 25 18 CH3 22 12 20 28 26 11 17 N 19 13 16 O H CH3 H 1 9 14 H 2 H 10 8 15 H H 3 7 5 4 6 spirosolane (the CAS name requires the chirality at C-22 to be specified)

18 19 N 2 1 17 H 20 16 6 3 15 7 H 4 8 14 5 21 9 N 13 H H 12 22 10 11 O 23 H 24 strychnidine

16 O-CH3 17 H 4 H CH3 3 12b N 2 5 15 1 12a 6 O 11 12 6a OH 14 O O 10 8a 7 13 9 8 tazettine (named systematically by CAS)

1 2 7 9 H3C N 8 3 6 4 5 tropane (named systematically by CAS) 5 4 16 6 3

7 2 1 NH 17 18 O 8 H 15 12’ 9 11’ 13’ 14 10 10’ 14’ 9’ 13 11 12 H 15’ O 8’ 18’ 17’ 1’ HN 2’ 7’

3’ 6’ 16’ 4’ 5’ tubocuraran (named systematically by CAS)

9 7 8 10 6

5 11 N 13 4 14 12 H 16 17 3 CH2-CH3 1 2 H 15 H H H 13’ 1’ N HN2’ 12’ 11 ’ 10’ 3 ’ 5’ 6 4’ ’ 9’

7’ 8’ tubulosan (named systematically by CAS)

21 CH3 HN 26 27 18 H 28 CH CH 3 3 22 25 20 13 H 17 H 11 12 23 24 19 H 16 CH3 H 14 1 9 2 15 10 8 H H 3 5 7 4 6 veratraman (named systematically by CAS)

OH 5’ 6’ 20’ 21’ 7’ CH -CH N 4’ 2 3 8’ 2 3’ 8 7 11’ 19’ ’ 10’ 9’ 12’ H 9 6 N 20 21 18’ 1’ 10 19 5 CH2-CH3 16’ 17’ 13 H ’ 15 N ’ 22’ 14 11 14’ H 15 H 4 12 O-CO-CH CH3-O O 13 2 3 3 23’ 1 CO-O-CH3 23 24 CH3-O 16 18 N H OH 25 17 CH3 22 vincaleukoblastine 6 5

9 7 4 19 8 H N 10 3 18 1 2 11 13 N 16 12 17 CH2-CH3 14 15 20 21 vincane (CAS name based on eburnamenine)

CH3 4 21 H N H 20 5 19 6 16 15 9 CH3 7 8 H H 18 10 CH 17 3 14 1 2 3 11 13 N 12 H vobasan

8’ 7 ’ H 9’ N 6 24’ 10’ ’ O 19’ 5’ 20’ 21’ 14’ 11’ 12’ H 15’ 4’ 2 3 13’ ’ ’ H 16’ 1’ 22 18’ N OH 22’ O 17’ 21 H O-CH3 23’ 7 6 20 25 ’ 8 5 4 3 9 N H CO-O-CH3 19 23 12 10 2 11 13 1 NH 14 18 15 17 16 vobtusine (named systematically by CAS)

10 9 6 11 8 7 5

12 13 1 4 3 N N 2 21 H H H 20 14 15 19 H 16 18 17 yohimban 2. Steroids

18 12 CH3 17 11 19 13 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 androstane

O

O 24 23 21 H 18 22 12 CH3 20 11 H 19 13 17 CH H 16 1 3 9 14 2 10 8 15 H H 3 7 5 4 6 bufanolide

241 H CH3 21 H 22 26 H3C CH3 24 18 20 23 25 12 CH3 H CH3 11 27 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 campestane (named by CAS as a stereoisomer of ergostane in which the locant 241 is 28)

O

O 23 H 21 22 18 20 12 CH3 H 11 19 13 17 CH H 1 3 9 14 16 2 10 8 H H 3 5 4 6 cardanolide

21 H 22 24 H3C CH3 18 20 23 12 CH3 H 11 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 cholane 21 H 22 24 26 H3C CH3 18 20 23 25 12 CH3 H CH3 11 27 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 cholestane

241 H CH3 21 H 22 26 H3C CH3 24 18 20 23 25 12 CH3 H CH3 11 27 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 ergostane

18 12 CH3 17 11 13 H H 1 9 14 16 2 10 8 15 H H 3 7 5 4 6 estrane

21 27 CH CH3 H 3 23 25 18 22 12 CH3 20 CH 24 3 11 H 26 19 13 17 O CH H 16 1 3 9 14 2 H 10 8 15 H H 3 7 5 4 6 furostan

12 H 17 11 13 H H 16 1 9 14 2 10 8 15 H H 3 7 5 4 6 gonane H H 221 CH3 21 H 26 H3C CH3 22 24 18 20 23 25 12 CH3 H CH3 CH3 11 231 27 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 gorgostane (for CAS the locants 221, 231, and 241 are 34, 33, and 28, respectively)

241 242 H CH2-CH3 21 22 H3C CH3 18 24 26 20 23 25 12 CH3 H CH3 11 27 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 poriferastane (named by CAS as a stereoisomer of stigmastane in which the locants 241 and 242 are 28 and 29, respectively.)

20 21 18 CH2-CH3 12 CH3 H 11 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 7 5 4 6 pregnane

27 21 26 CH3 25 CH3 H O 18 22 12 CH3 20 24 11 H 19 13 17 O 23 CH H 16 1 3 9 14 2 H 10 8 15 H H 3 7 5 4 6 spirostan (the CAS name requires the chirality at C-22 to be specified)

241 242 H CH2-CH3 21 H 22 H3C CH3 18 24 26 20 23 25 12 CH3 H CH3 11 27 19 13 17 CH H 1 3 9 14 16 2 10 8 15 H H 3 5 7 4 6 stigmastane 3. Terpenoids

16 CH3 17 15 12 CH CH3 11 20 13 H CH H 1 3 9 14 2 10 8 H 5 3 4 7 H 6 H3C CH3 18 19 abietane (named systematically by CAS)

14 H CH3 H 2 9 10 1 3 8 12 5 11 CH3 6 7 4 CH CH3 15 H CH3 13 ambrosane (named systematically by CAS)

1 H 9 2 8 10 5 7 3 4 6 H 12 CH3 CH3 15 11 H3C H H 14 CH3 13 aristolane (named systematically by CAS)

17 12 CH3 11 20 H CH 14 16 1 3 9 13 2 15 10 8 H 5 3 4 7 H 6 H3C CH3 18 19 atisane

17 CH3 12 13 11 20 16 CH 14 1 3 9 2 15 10 8 H 5 3 4 7 H 6 H3C CH3 18 19 beyerane (CAS name based on kaurane) 15 CH3 10 2 1 9 3

8 6 4 7 CH3 5 14

11 H3C CH3 12 13 bisabolane (named systematically by CAS)

10 CH3 1 6 2 7 H3C CH3 9 8 5 3 4 bornane (named systematically by CAS)

15 H CH3 2 H 3 10 9 1 14 4 6 H3C 7 8 H 5 H 11 12 H CH CH3

CH3 13 cadinane (named systematically by CAS)

10 CH3 3 2 4

1 5 6 H3C 7 8 CH3 9 carane (named systematically by CAS)

18’ 4’ 16 17 19 20 H3C 5’ CH CH 3’ H3C CH3 3 3 7 11 15 12 8 14’ ’ 10’ ’ 6 13’ 9’ 2 1 9 13 6’ 2’ CH 8 10 12 14 15 11 7 1’ 3 ’ ’ ’ 17’ 3 CH3 CH3 CH3 5 16 CH3 20’ 19’ ’ 4 18 β,φ-carotene

16 17 19 20 CH CH H3C CH3 3 3 7 11 15 12 8 16 14’ ’ 10’ ’ 6’ 4’ 2’ ’ 6 13’ 9’ 5’ CH3 2 1 9 13 8 12 14 15’ 11’ 7’ 3’ 1’ 3 CH3 CH3 CH3 CH3 5 17 CH3 20’ 19’ 18’ ’ 4 18 β,ψ-carotene 16 17 19 20 16’ 17’ CH CH H3C CH3 3 3 H3C CH3 7 11 15 12 8 14’ ’ 10’ ’ 6’ 6 13 9 ’ 9’ 5’ 2 1 13 1’ 2’ 8 10 12 14 15’ 11’ 7’ H3C 3 CH3 CH3 4 3 5 20 19 18’ ’ ’ CH3 ’ ’ 4 18 ε,κ-carotene

18 4’ ’ 16 17 19 20 3’ CH3 CH CH 5’ H3C CH3 3 3 7 11 15 12 8 14’ ’ 10’ ’ 6 13’ 9’ 2 1 9 13 6’ 2’ CH 8 10 12 14 15’ 11 7 1’ 3 ’ ’ 17’ 3 CH3 CH3 CH3 5 20 19 CH3 ’ ’ 16’ 4 18 ε,χ-carotene

Note: There are 28 possible carotene parent structures of which four are illustrated above. The 28 are derived from all permutations of the following seven end groups:

16 17 16 17 16 17 16 H3C CH3 H3C CH3 H3C CH3 CH3 17 6 6 6 H3C 2 6 2 1 2 1 2 1 1

3 3 3 3 5 5 5 5 CH3 CH3 CH2 CH3 4 18 4 18 4 18 4 18 β (beta) ε (epsilon) γ (gamma) φ (phi)

16 16 17 CH3 H3C CH3 17 18 17 CH CH H3C 2 6 CH3 3 3 1 18 1 3 2 5 16 1 5 18 6 H3C 4 5 2 6 H3C 3 3 4 4 χ (chi) κ (kappa) ψ (psi)

14 13 CH3 CH3 1 12 11 9 2 3 H3C 4

10 8 6 7 5

CH3 15 caryophyllane (named systematically by CAS)

12 H 10 9 H3C H 15 8 2 1 11 CH3 3 7 5 H 6 4 CH3 H 14 CH3 13 cedrane (named systematically by CAS) 21 H 22 24 26 H3C CH3 20 25 12 H 23 H 11 CH3 19 18 13 17 27 CH CH 1 3 9 3 14 16 2 10 8 15 H CH3 5 30 3 4 7 H 6 H3C CH3 28 29 dammarane

11 15 H CH H C 3 1 3 H 2 9 10 8 CH3 5 12 3 4 7 H 6 H3C CH3 13 14 drimane (named systematically by CAS)

1 H 9 2 8 10 12 5 7 H CH 3 4 3 CH 6 11 H CH3 15 CH CH3 3 14 13 eremophilane (named systematically by CAS)

15 1 CH3 2 9 8 10 12 5 7 H CH 3 4 3 CH H H 6 11 CH3 CH3 14 13 eudesmane (named systematically by CAS)

CH3

CH3

CH3 fenchane (named systematically by CAS) 20 19 21 H H 30 12 18 22 CH 11 3 25 26 13 17 CH CH3 CH3 CH3 3 1 9 14 28 29 16 2 10 8 15 H CH3 5 27 3 4 7 6 H3C CH3 23 24 gammacerane

15 H CH3

2 9 1 10 3 8 4 7 5 12 6 11 CH3 H CH3 H CH 14 CH3 13 germacrane (named systematically by CAS)

6 5 7 4 . 4b 4a 11 3 8

10a 9 2 9a 10 1 H gibbane

20 H 11 12 H3C H H . 13 2 14 10 9 H 1 15 3 5 8 CH3 4 16 17 7 H3C H 6 18 CH3 19 grayanotoxane

14 H CH3 H 2 9 10 1 3 8 5 4 7 12 H 6 11 CH3 H CH3 H CH 15 CH3 13 guaiane (named systematically by CAS) 12 CH3 2 H 11 10 3 1 9 6 4 7 H3C 8 13 5 H H3C CH3 14 15 himachalane (named systematically by CAS)

29 19 20 CH3 H H 21 22 12 18 11 CH3 25 26 13 17 H 30 CH3 CH3 CH3 1 9 14 28 16 2 10 8 15 H CH3 5 27 3 4 7 H 6 H3C CH3 23 24 hopane (CAS name based on gammacerane)

13 CH3 14 6 3 CH3 4 5 7 CH3 2 15 8 11 1 10 9

CH3 12 humulane (named systematically by CAS)

12 13 17 CH 11 3 20 CH 14 16 1 3 9 H 2 15 10 8 H 5 3 4 7 H 6 H3C CH3 18 19 kaurane (named by CAS ent-stereoisomer)

12 14 13 15 11 17 CH3 1 CH3 H 9 H CH3 2 16 10 8 H CH3 5 20 3 4 7 H 6 H3C CH3 18 19 labdane (named systematically by CAS) H 21 22 24 26 H3C CH3 18 20 23 25 CH3 12 H 11 CH3 19 13 17 27 CH H 16 1 3 9 14 2 10 8 H CH3 5 30 3 4 7 H 6 H3C CH3 28 29 lanostane

29 30 H3C 20 CH3 H 21 H 19 12 18 22 11 17 25 26 13 28 CH CH H CH 1 3 9 3 14 3 16 2 10 8 15 H CH3 5 27 3 4 7 H 6 H3C CH3 23 24 lupane

7 CH3 1 6 2

5 3 4

8 H3C CH3 9 10 p-menthane (named systematically by CAS)

29 30 H3C CH3

19 20 21 H 12 18 11 17 22 25 26 13 1 CH3 CH3 H CH3 9 14 28 16 2 10 8 15 H CH3 3 5 27 4 7 H 6 H3C CH3 23 24 oleanane 16 H 21 H3C 17 19 CH3 25 15 18 20 H3C 8 9 H H H CH3 7 10 14 22 H 13 6 11 5 2 1 12 CH3 3 23 4 H

H CH3 24 ophiobolane (named systematically by CAS)

21 12 CH3 11 19 20 H 13 CH3 CH3 1 9 14 2 15 10 8 H H 5 7 3 4 16 O 6 H H 17 H CH3 18 picrasane

17 12 CH3 11 20 13 CH2-CH3 CH H 15 16 1 3 9 14 2 10 8 5 H 3 4 7 6 H H3C CH3 18 19 pimarane (named systematically by CAS)

10 CH3 2 1 3 7 6 H3C 4 8 5 CH3 9 pinane (named systematically by CAS)

12

17 11 13 CH H 1 3 9 14 2 10 8 H 5 3 4 7 H 6 H3C CH3 15 16 podocarpane (named systematically by CAS) 21 H 24 26 H3C 22 CH3 H 20 23 25 12 17 11 CH3 19 18 13 27 CH3 CH3 16 1 9 14 2 10 8 15 H CH3 5 30 3 4 7 H 6 H3C CH3 28 29 protostane (named by CAS as a stereoisomer of dammarane)

16 17 19 20 CH CH H3C CH3 3 3 7 11 15 6 CHO 2 1 9 13 8 10 12 14

3 5 CH3 4 18 retinal

17 12 CH3 11 13 CH2-CH3 H H 15 16 1 9 14 10 8 CH3 5 20 3 4 7 H 6 H3C CH3 18 19 rosane (named systematically by CAS)

19 18 H H 10 9 CH H C 3 7 3 16 11 6 12 CH3 8 13 15 3 5 1 CH3 4 17 14 H H CH3 H 2 20 taxane (named systematically by CAS)

CH3 4 5 3

6 1 2

7 H3C CH3 8 9 thujane (named systematically by CAS)

H 1 H H C 10 O 2 3 9 13 11 H C 3 3 6 12 8 7 4 5 H3C 15 CH3 14 trichothecane 30 H CH H 3 29 H3C 20 21 19 H 12 18 11 17 22 25 26 13 1 CH3 CH3 H CH3 9 14 28 2 16 10 8 15 H CH3 3 5 27 4 7 H 6 H3C CH3 23 24 ursane

4. Miscellaneous

18 2 19 1 17 3 21 16 N N 4 24 H 15 5 23 22 14 N N 6 13 7 11 9 12 10 8 21H-biline

H 1 S 7 2 6 8 N 3 5 O 4 cepham (named systematically by CAS)

5 7 3 6 4 8 2 N 9 1 N 22 21 10 24 19 NH 23 N 11 18 12 16 17 14 15 13 corrin

5’ 6’ 4’ 8 1 8a O 2 3’ 7 1’ 2’ 6 4a 3 5 4 flavan (named systematically by CAS) 8 1 8a O 7 2

2’ 6 1 4a 3 ’ 3’ 5 4

6’ 4’ 5’ isoflavan (named systematically by CAS)

9 9’ H3C CH3 5 6 6’ 5’ 8 8’ 4 4 1 ’ 7 7’ 1’ 3 2 2’ 3’ lignane [only through a 8,8′ (β,β′) linkage] (named systematically by CAS)

8 1 8a O 7 2

6 3 4a 5 4 1’ 6’ 2’

5’ 3’ 4’ neoflavan (named systematically by CAS)

8 7 7’ 8’ 1 2 2’ 1’ H3C CH3 9 9’ 6 6’ 3 3’

5 4 4’ 5’ 3,3′-neolignane [and other structures not connected through a 8,8′) (β,β′) linkage] (named systematically by CAS)

H 1 6 S 5 2 7 N 4 O 3 penam (named systematically by CAS)

3 5 7 4 6 2 8

1 NH N 9 21 22 20 10 23 24 19 N HN 11 18 12 16 14 17 15 13 21H,23H-porphyrin (named by CAS on the basis of the parent name porphine) 1 H 7 3 9 5 6 4 2 CH3 8 10 12 CH3 14 16 11 18 20 13 15 17 19 H prostane

H 9 7 5 3 1 6 4 2 CH3 10 8 12 11 CH3 O 14 16 18 20 13 17 19 H 15 thromboxane (named systematically by CAS)

!