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Eugene E. Van Tamelen 12/12/15 Baran Group Meeting Julian Lo Eugene E. van Tamelen 12/12/15 Biography Research Interests Known as Gene among friends, but vT among colleagues 1. Valence bond isomerism (e.g., Dewar benzene) Born July 20, 1925 in Zeeland, MI 2. Polyene cyclizations and lanosterol biosynthesis Died Decemeber 12, 2009 (84) of cancer 3. Nitrogen fixation and other methodology 4. Alkaloid total synthesis Education 5. Structural elucidation via degradation studies A.B. from Hope College (Gerrit van Zyl) in 1947 •First undergrad to publish a paper, total of 6 publications Top Cited Publications E Me Me E 1. Bioorganic Chemistry - Sterols and Acyclic Terpene Me Me Terminal Epoxides. Acc. Chem. Res. 1968, 1, 111. + Na + O N 2 (237 citations) O2N Br E 2 2 E •Gene van Tamelen Prize for Creativity in the Sciences 2. Enzymatic Conversion of Squalene 2,3-Oxide to •van Tamelen Plaza Lanosterol and Cholesterol. J. Am. Chem. Soc. 1966, 88, 4752. (219 citations) Ph.D. from Harvard (Gilbert Stork) in 1950 O O 3. Design and Development of an Organic-Inorganic Synthesis of cantharidin System for Chemical Modification of Molecular O (J. Am. Chem. Soc. 1951, 4501) Nitrogen Under Mild Conditions. Acc. Chem. Res. Me O (J. Am. Chem. Soc. 1953, 384) 1970, 3, 361. (127 citations) Me Academic Career Mentored more than 200 doctoral students and postdocs 1950: Joined University of Wisconsin-Madision Barry Sharpless (Ph. D, now at Scripps) 1959: Full professor Kenneth S. Feldman (Ph.D, now at Penn State) "Sharpless! The only rule is 1962: Moved to Stanford Peter Dervan (post doc, now at Caltech) 'There are no rules!'" 1971: Founded the journal Bioorganic Chemistry 1972–1978: Chair of Stanford Chemistry Department 1987: Retired Architecture Aficionado Contemporaries (Influences?) at Stanford Owner of the first Frank Lloyd Wright- William S. Johnson designed Marshall Erdman Carl Djerassi prefabricated house, now known as the James P. Collman van Tamelen House. Henry Taube •Spent $55,000 (base price: $16,400) Designed two family vacation homes •Pajaro Dunes on Monterey Bay •Caribbean island of St. Lucia Selected Awards and Honors George I. Haight Travelling Research Fellowship, 1957 ACS Award in Pure Chemistry, 1961 Guggenheim Fellowship, 1964 Leo Hendrik Baekeland Award, 1965 Professor Extraordinarious (University of Groningen), 1967 Automobile Enthusiast Elected to the National Academy of Sciences, 1968 Childhood dream was to design cars, but ACS Award for Creative Work in Synthetic Organic Chemistry, 1970 eventually settled for just owning them. Honorary Sc.D. from Hope College, 1970 Honorary Sc.D. from Bucknell University Drove a classic Excalibur and a Rolls-Royce. One of the 2,000 best scientists of the 20th century by IBC Member of the Rolls-Royce Owners' Club. Baran Group Meeting Julian Lo Eugene E. van Tamelen 12/12/15 1. Valence Bond Isomerism Although sometimes bizzare reactivity was observed instead of the desired isomerism (J. Am. Chem. Soc. 1965, 4964). First synthesis of Dewar benzene (J. Am. Chem. Soc. 1963, 3297). O O O Li 0 H H H H hν Li PhLi + 0 OH Ac2O hν Pb(OAc)4 2 Li O O Et2O Li (>80%) OH 100 °C Et2O pyridine 43–45 °C H O H H O H O O reduced P can also be made Substituted furans were found to undergo valence bond isomerism to give cyclopropenes (ca. 20%) via electrolytic (J. Am. Chem. Soc. 1968, 3894). 2 tBu H tBu hν OH direct photolysis of decarboxylation tBu hν 1 OH diacid gave retro 6π (Tetrahedron Lett. 3 + + 1968, 5117) tBu tBu pentane O O tBu O (50% RSM) tBu O O tBu 4% 9% 9% Dewar benzene is isolable because it's more thermally stable than one might expect. 1,2-H • trans But: shift H H Δ H tBu H H hν H or retro 4π H tBu O tBu retro 4π tBu O tBu conrot. H disrot. H O tBu 2,3 homolysis 1,3 homolysis Dewar bezene behaves as a non-aromatic olefin (J. Am. Chem. Soc. 1967, 3922). In certain cases, other types of rearrangements occurred. HO OH Br Br O OsO4 Br2 tBu tBu Me + hν (26%) 0 °C Me Mechanism? HO OH (97%) Br Br pentane 3 : 7 tBu O tBu (ca. 95%) tBu Adducts of Dewar benzene can rearrange, but do not readily isomerize to the parent Kekule benzene (J. Am. Chem. Soc. 1971, 6102). Photolysis of the trityl cation in the presence of O2 led to more rearranged products (J. Am. Chem. Soc. 1970, 4123). mCPBA 115 °C Ph O O O AcOH 3 Ph OAc O Et2O dodecane Ph Ph H2SO4 Ph Ph O (ca. 75%) + + O Ph Ph OH H2O O Ph Ph O Ph Ph O O2, hν H Cl 3 (11%) (30%) (37%) Cl3C OEt Cl hν Cl O2 NaOMe Cl (30%) AcOH Cl Cl Ph Ph Ph Ph Ph radical O Charged aromatic species also underwent isomerization upon photolysis (J. Am. Chem. Soc. Used by Barton to Ph 1,2-shift 1968, 1372). effect a stepwise O O H HO O H H radical [4+2] O O O 5% aq H2SO4 H2O cycloaddition of O H BF + 2 Ph Ph Ph 4 hν (58%) (J. Chem. Soc. Chem Comm. 1972, 447). Ph H H 2 O H – H+ O O O Baran Group Meeting Julian Lo Eugene E. van Tamelen 12/12/15 Although not in synthetically useful yields, the photolysis of enolates generated epoxides van Tamelen was also interested in other non-benzenoid aromatics (J. Am. Chem. Soc. (J. Am. Chem. Soc. 1970, 5798). 1958, 4405). Et Et O O O OH O OEt NaNH2 OH Raney Ni + + HO Me Me NH , hν Et Me Et Me aq. NaOH TsOH 3 Et Et OH OH OH 2% 0.2% major H2 (1400 psi) EtOH HO O (86%) O hν 50 °C +H+ H O O (86%) O O Me Me A steel hydrogenation bomb was charged 1. LiAlH4 O O O with... 3 teaspoonsful of W-1 Raney nickel. 2. TsCl, pyr (56% overall) Me Me Me Me Et Me O O O O O +H+ SeO2 NaOH Et Me AcOH (66%) OTs van Tamelen was the first to propose the correct structure of photosantonic acid after numerous H2O degradation studies, which was later confirmed by X-ray crystallography (J. Am. Chem. Soc. 1959, 1666; X-ray of ester: Sheldon, Acta Cryst. 1982, 649). Completed his synthesis of colchicine one month after Eschenmoser's (J. Am. Chem. Soc. Me Me 1959, 6341 and Tetrahedron 1961, 8). Me Me MeO O MeO Me H hν hν 1. , tBuOK H H CN CO Me 1. KOH O Me HO MeO 2 Me Me MeO 2. BrCH CO Me, Zn0 2. DCC, pyr Me O O 2 2 MeO OH O O O MeO (14% overall) 3. CH2N2 CN (38% overall) O O O other diastereomer was santonin lumisantonin photosantonic acid major product (1:2) MeO MeO Although van Tamelen proposed a mechanism for the conversion of lumisantonin to CO2Me photosantonic acid, a more plausible mechanism was suggested by Chapman (J. Am. Chem. MeO Na0, NH Soc. 1963, 3028). 3 MeO 1. Cu(OAc) MeO O O 2 (10%) MeO Me Me Me Me 2. TsOH (40% overall) OH Me Me O 3. NBS, Δ O O O OH H H H 1. NBS, (BzO) Me MeO MeO 2 Me Me 2. NaN3 O O O 3. H2, Pd/C MeO CH N MeO O O O 2 2 4. 1 M HCl lumisantonin MeO (70%) MeO (7% overall) Me Me Me Me OH OMe MeO O O O Me Me 1:1 mixture of regioisomers NH2 H H2O H H HO other regioisomer did not react MeO Me Me retro 6π Me O MeO O O O O OH O O O photosantonic acid isolated O trimethylcolchicinic acid Baran Group Meeting Julian Lo Eugene E. van Tamelen 12/12/15 2. Polyene Cyclizations and Lanosterol Biosynthesis However, using purely chemical means to cyclize 2,3-oxidosqualene resulted in products bearing a 5-membered C ring instead of a 6-membered one (J. Am. Chem. Soc. 1966, 5937). At the outset of this work, it was not known how the polyene cyclization that Nature uses to convert squalene into lanosterol is initiated (Acc. Chem. Res. 1968, 111). 2,3-oxidosqualene R R = R TiCl4 PhH HO R enzyme H HO HO [O] HO + OH HO O van Tamelen O proposed: HO This raised the possibility that the lanosterol bisynthesis proceeds by way of a 5-membered C O ring intermediate, which was initially supported by modifying the 2,3-oxidosqualene precursor (J. Am. Chem. Soc. 1967, 7150). Conditions for the selective oxidation of the terminal olefin in various polyenes (Tetrahedron R Lett. 1962, 121). OH O rat liver microsomes NBS Br H2O glyme base HO lanosterol (81%) O HO O Br lanosterol biosynthesis?: R R R The selectivity of the bromohydrin formation was influenced by the solvent composition R (Tetrahedron Lett. 1967, 2655). OMe glyme, H2O pet. ether, AcOH [O] c favored in more a: 95% a: 81% polar solvents: b: 5% b: 19% greater selectivity H b c: 0% c: 0% H a vs. favored in less polar solvents: b a: 98.5% a: 62% lower selectivity However, upon removing the C-15 Me group to rid the substrate of electronic bias, the enzyme b: 1.5% b: 38% did not favor formation of a 5-membered ring. This led to the full mechanistic picture of a 2 lanosterol bisynthesis (J. Am. Chem. Soc. 1982, 6479 and J. Am. Chem. Soc. 1982, 6480)! Experiments done in collaboration with Clayton showed that 2,3-oxidosqualene was a genuine intermediate in the biosynthesis of lanosterol (J.
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