Read dykhuizen-ref.pdf text version

Abe, I.; Rohmer, M.; Prestwich, G.D. "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes" Chem. Rev. 1993, 93, 2189-2206. Bartlett, P.A.; Johnson, W.S. "Stereospecific total synthesis of estrone via cationic olefinic cyclization" J. Am. Chem. Soc. 1973, 95, 7501-7502. Bartlett, P.A.; Johnson, W.S.; Elliott, J.D. "Asymmetric synthesis via acetal templates. 3. On the stereochemistry observed in the cyclization of chiral acetals of polyolefinic aldehydes; formation of optically active homoallylic alcohols" J. Am. Chem. Soc. 1983, 105, 2088-2089. Bartlett, W.R.; Johnson, W.S. "Nonenzymic biogenetic-like olefin cyclization. Cyclization of 1-methyl-6(trans,trans-7,11-dimethyl-3,7,11-dodecatrienyl)-2-cyclohexen-1-ol" J. Am. Chem. Soc. 1974, 96, 25492556. Bender, J.A.; Blize, A.E.; Browder, C.C.; Giese, S.; West, F.G. "Highly diastereoselective cycloisomerization of acyclic trienones. The interrupted Nazarov reaction" J. Org. Chem. 1998, 63, 24302431. Bender, J.A.; Arif, A.M. and West, F.G. "Nazarov-initiated diastereoselective cascade polycyclization of aryltrienones" J. Am. Chem. Soc. 1999, 121, 7443-7444. Burke, S.D.; Kort, M.E.; Strickland, M.S.; Organ, H.M.; Silk, L.A.III "Enantioselective synthesis of nagilactone F via vinylsilane-terminated cationic cyclization" Tetrahedron Lett. 1994, 35, 1503-1506. Corey, E.J.; Wood Jr., H.B. "A new strategy for stereocontrol of cation-olefin cyclization. The first chemical emulation of the A/B-trans-9,10-syn-folding pathway of steroid biosynthesis from 2,3oxidosqualene" J. Am. Chem. Soc., 1996, 118, 11982-11983. De la Torre, M.C.; Sierra, M.A. "Comments on recent achievements in biomimetic organic synthesis." Angew. Chem. Int. Ed. 2004, 43, 160-181. Dijkink, J.; Speckamp, W.N. "Simultaneous and stereospecific formation of two C-C bonds via acylimmonium cyclisation" Tetrahedron Lett. 1977, 18, 935-938. Edstrom, E.; Livinghouse, T. "Formation of episulfonium ions from alkenes. Application to the synthesis of higher order carbocycles via episulfonium ion initiated polyene cyclizations" J. Org. Chem. 1987, 52, 949-951. Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. "Zur kenntnis der triterpene: Eine stereochemische interpretation der biogenetischen isoprenregel bei den triterpenen" Helv. Chim. Acta. 1955, 38, 1890-1904. Eschenmoser, A.; Felix, D.; Gut, M.; Meier, J.; Stadler, P. "Some aspects of acid-catalysed cyclizations of terpenoid polyenes" In Ciba Foundation Symposium on the Biosynthesiis of Terpenes and Steroids; Wolstenholme, G.E.W; O'Conner, M., Eds; J. and A. Churchill: London, 1959, pp 217-230. Fish, P.V.; Johnson, W.S.; Jones, G.S; Tham, F.S.; Kullnig, R.K. "Chiral acetal-initiated asymmetric pentacyclization. Enantioselective synthesiis of 18 (H)-oleananes" J. Org. Chem. 1994, 59, 6150-6152. Fleming, I.; Pearce, A.; Snowden, R.L. "Controlling the outcome of a carbonium ion reaction: the use of a trimethylsilyl group to dictate the formation of a specific olefin" J. Chem. Soc., Chem. Commun. 1976, 182-183. Garst, M.E.; Cheung, Y-F; Johnson, W.S. "Biomimetic polyene cyclizations. Trapping of the resultant carbocation by an internal nucleophile" J. Am. Chem. Soc. 1979, 101, 4404-4406.

Heathcock, C.H. "Nature knows best: An amazing reaction cascade is uncovered by design and discovery" Proc. Natl. Acad. Sci., U.S.A. 1996, 93, 14323-14327. Heinemann, C.; Xing, X.; Warzecha, K.D.; Ritterskamp, P.; Gorner, H.; Demuth, M. "An asymmetric induction principle and biomimetics with photons via electron transfer" Pure Appl. Chem. 1998, 70, 21672176. Heinemann, C.; Demuth, M. "Short biomimetic synthesis of a steroid by photoinduced electron transfer and remote asymmetric induction" J. Am. Chem. Soc. 1999, 121, 4894-4895. Hoshino, T ; Sato, T. "Squalene­hopene cyclase: catalytic mechanism and substrate recognition" Chem. Commun., 2002, 4, 291 ­ 301. Ishibashi, H.; Ishihara, K.; Yamamoto, H. "Chiral proton donor reagents: tin tetrachloride-coordinated optically active binaphthol derivatives" Chem. Record 2002, 2, 177-188. Ishihara, K.; Nakamura, S.; Yamamoto, H. "The first enantioselective biomimetic cyclization of polyprenoids" J. Am. Chem. Soc. 1999, 121, 4906-4907. Johnson, W.S.; Crandall, J.K. "Olefinic cyclizations. VII. Formolysis of cis and trans-5,9-decadienyl pnitrobenzenesulfonate and some isomeric monocyclic esters" J. Org. Chem. 1965, 30, 1785-1790. Johnson, W.S. and Kinnel, R.B. "Stereospecific tricyclization of a polyolefinic acetal" J. Am. Chem. Soc. 1966, 88, 3861-3862. Johnson, W.S.; Semmelhack, M.F.; Sultanbawa, M.U.S.; Dolak, L.A. "A new approach to steroid total synthesis. A nonenzymic biogenetic-like olefin cyclization involving the stereospecific formation of five asymmetric centers" J. Am. Chem. Soc. 1968, 90, 2994-2996. Johnson, W.S.; Wiedhaup, K.; Brady, S.F.; Olson, G. "The nonenzymic, biogenetic-like cyclization of a tetraenic acetal" J. Am. Chem. Soc. 1968, 90, 5277-5279. Johnson, W.S.; Harbert, C.A.; Stipanovic, R.D. "Asymmetric induction of an olefinic acetal cyclization" J. Am. Chem. Soc. 1968, 90, 5279-5280. Johnson, W.S.; Gravestock, M.B.; McCarry, B.E. "Evidence concerning the bishomocyclobutenium dication as a solvolytic intermediate" J. Am. Chem. Soc. 1971, 93, 2994-2996. Johnson, W.S.; DuBois, G.E. "Biomimetic polyene cyclizations. Asymmetric induction by a chiral center remote from the initiating cationic center. 11--methylprogesterone" J. Am. Chem. Soc. 1975, 98, 10381039. Johnson, W.S. "Biomimetic polyene cyclizations" Bioorg. Chem. 1976, 5, 51-98. Johnson, W.S.; Bunes, L.A. "Participation of the styrene group as a terminator of biomimetic polyene cyclizations. Formation of the trans-8-methylhydrindan ring system" J. Am. Chem. Soc. 1976, 98, 55975602. Johnson, W.S.; Hughes, L.R.; Kloek, J.A.; Niem, T.; Shenvi, A. "Biomimetic polyene cyclizations. Participation of the phenylacetylenic group as a terminator and the formation of C/D cis steroidal products" J. Am. Chem. Soc. 1979, 101, 1279-1281. Johnson, W.S.; Hughes, L.R.; Carlson, J.L. "Biomimetic polyene cyclization. A comparison of the phenylacetylenic and styryl terminators in influencing the stereochemistry of processes leading to steroidal products" J. Am. Chem. Soc. 1979, 101, 1281-1282.

Johnson, W.S.; Daub, G.W.; Lyle, T.A.; Niwa, M. "Vinyl fluoride function as a terminator of biomimetic polyene cyclizations leading to steroids" J. Am. Chem. Soc. 1980, 102, 7800-7802. Johnson, W.S.; Telfer, S.J.; Cheng, S.; Schubert, U. "Cation-stabilizing auxiliaries: a new concept in biomimetic polyene cyclization" J. Am. Chem. Soc. 1987,109, 2517-2518. Johnson, W.S.; Lindell, S.D.; Steele, J. "Rate enhancement of biomimetic polyene cyclizations by a cationstabilizing auxiliary" J. Am. Chem. Soc. 1987, 109, 5852-5853. Johnson, W.S. "Fifty years of research: A tribute to my co-workers" Tetrahedron 1991, 47, xi-1. Johnson, W.S.; Chenera, B.; Tham, F.S.; Kullnig, R.K. "Cation-stabilizing auxiliaries in polyene cyclizations. 4. The fluorine atom as a cation-stabilizing auxiliary in biomimetic polyene cyclizations. 1. Background and exploratory experiments" J. Am. Chem. Soc. 1993, 115, 493-497. Johnson, W.S.; Plummer, M.S.; Reddy, S.P.; Bartlett, W.R. "Cation-stabilizing auxiliaries in polyene cyclizations. 7. The fluorine atom as a cation-stabilizing auxiliary in biomimetic polyene cyclizations. 4. Total synthesis of dl--amyrin" J. Am. Chem. Soc. 1993, 115, 515-521. Johnson,W.S; Bartlett, W.R.; Czeskis, B.A.; Gautier, A.; Lee, C.H.; Lemoine, R.; Leopold, E.J.; Luedtke, G.R.; Bancroft, K.J. "The fluorine atom as a cation-stabilizing auxiliary in biomimetic polyene cyclizations: total synthesis of dl-dammarenediol" J. Org. Chem. 1999, 64, 9587-9595. Julia, M. "Free-radical cyclizations" Acc. Chem. Res. 1971, 4, 386-392. Langdon, R.G.; Bloch, K. "The biosynthesis of squalene and cholesterol" J. Am. Chem. Soc. 1952, 74, 1869-1870. Lesburg, C.A.; Zhai, G.; Cane, D.E.; Christianson, D.W. "Crystal structure of pentalene synthase: mechanistic insights on terpenoid cyclization reactions in biology" Science 1997, 277, 1820-1824. Manitto, P. "The Isoprenoids" In Biosynthsis of Natural Products; Ellis Harwood: Chichester, 1981; pp. 215-313. Nakamura, S.; Ishihara, K.; Yamamoto, H. "Enantioselective biomimetic cyclization of isoprenoids using Lewis acid-assisted chiral Brønsted acids: abnormal claisen rearrangements and succesive cyclizations" J. Am. Chem. Soc. 2000, 122, 8131-8140. Ohsawa, T.; Takagaki, T.; Haneda, A.; Oishi, T. "Dissolving metal reduction by crown ether­hydrogenolysis of alkyl fluorides" Tetrahedron Lett. 1981, 22, 2583-2586. Robinson, R. "A synthesis of tropinone" J. Chem. Soc. 1917, 111, 762-768. Robinson, R. "A theory of the mechanism of the phytochemical synthesis of certain alkaloids" J. Chem. Soc. 1917, 111, 876-899. Romero, A.G.; Leiby, J.A.; Mizak, S.A. "Synthesis of an azasteroid using an acyl iminium ion-initiaterd tandem cyclization" J. Org. Chem. 1996, 61, 6974-6979. Schmid, R.; Huesmann, P.L.; Johnson, W.S. "Propargylsilane function as a terminator of biomimetic polyene cyclizations leading to steroids" J. Am. Chem. Soc. 1980,102, 5122-5123. Sorensen, E.J. "Architectual self-construction in nature and chemical synthesis" Bioorg. Med. Chem. 2003, 11, 3225-3228.

Starks, C.M.; Back, K.; Chappel, J.; Noel, J.P. "Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase" Science 1997, 277, 1815-1820. Stork, G.; Burgstrahler, A.W. "The stereochemistry of polyene cyclization" J. Am. Chem. Soc. 1955, 77, 5068. Sutherland, J.K. "Polyene Cyclizations" In Comprehensive Organic Synthesis; Trost, K.B.; Fleming, I., Eds.; Pergamon: New York, 1991; pp 341-377. Tanis, S.P.; Herrinton, P.M. "Furans in synthesis. 3. Furans as terminators in cationic cyclization" J. Org. Chem. 1983, 48, 4572-4580. Tchen, T.T.; Bloch, K. "On the mechanism of enzymatic cyclization of squalene" J. Biol. Chem. 1957, 226, 931. van Tamalan, E.E. "Biogenetic-type syntheses of natural products" Fortschr. Chem. Org. Naturst. 1961, 19, 242-290. van Tamelen, E.E. "Bioorganic chemistry: Sterols and acyclic terpene terminal epoxides" Acc. Chem. Res. 1968, 1, 111-120. van Tamelen, E.E.; Seiler, M.P.; Wierenga, W. "Biogenetic-type total synthesis. -amyrin, -amyrin and germanicol" J. Am. Chem. Soc. 1972, 94, 8229-8231. van Tamelen, E.E.; Hwu, J.R. "Direct total synthesis of traditional sterols by tricyclization of polyunsaturated cyclohexene oxides" J. Am. Chem. Soc. 1983,105, 2490-2491. Wendt, K.U.; Poralla, K.; Schulz, G.E. "Structure and function of a squalene cyclase" Science 1997, 277, 1811-1815. Wendt, K.U.; Schulz, G.E.; Corey, E.J.; Liu, D.R. "Enzyme mechanisms for polycyclic triterpene formation" Angew. Chem., Int. Ed. 2000, 39, 2812-2833. Willstätter, R. "Ueber monocyklische alkamine der tropingruppe und eine zweite synthese des tropidins" Liebigs Ann. Chem. 1903, 326, 1-42. Woodward, R.B.; Bloch, K. "The cyclization of squalene in cholesterol synthesis" J. Am. Chem. Soc. 1953, 75, 2023-2024. Nobel Lectures: Chemistry ; Elsevier Publishing: Amsterdam, 1964, pp 161-187.


4 pages

Report File (DMCA)

Our content is added by our users. We aim to remove reported files within 1 working day. Please use this link to notify us:

Report this file as copyright or inappropriate


You might also be interested in