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Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013

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Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013 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 .
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