Silicon in Synthesis. 21. Reagents for Thiophenyl-Functionalized Cyclopentenone Annulations and the Total Synthesis of (±)-Hirsutene

Journal of Organic Chemistry

Volumn 50, Issue 10, 1985, Pages 1621-1626

  Magnus, Philip ^a   Quagliato, Dominick ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845378722     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00210a013     Document Type: Article

References (18)

1. For a recent review article see: Magnus, P.; Sarkar, T.; Djuric, S. “Comprehensive Organometallic Chemistry”; Wilkinson, G., Ed.; Pergamon Press: New York; Vol. 7. Chan, T. H.; Fleming, I. Synthesis 1979, 761. Magnus, P. Aldrichimica Acta 1980, 13, 41.
2. Oshima, K.; Shimoji, K.; Takahashi, H.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1973, 95, 2694. Vlattas, I.; Veechia, L. D.; Lee, A. D. J. Am. Chem. Soc. 1976, 98, 2008. Cookson, R. C.; Parsons, P. J. J. Chem. Soc., Chem. Commun. 1976, 990. Cohen, T.; Mura, A. J., Jr.; Skull, W.; Fogel, E. R.; Ruffner, R. J.; Falck, J. R. J. Org. Chem. 1976, 41, 3218. Trost, B. M.; Crimmin, M. J.; Butler, D. J. Org. Chem. 1978, 43, 4549. Cookson, R. C.; Parson, P. J. J. Chem. Soc., Chem. Commun. 1978, 821. Harirchian, B.; Magnus, P. J. Chem. Soc., Chem. Commun. 1977, 522. Posner, G. H.; Tang, P-W. J. Org. Chem. 1978, 43, 4131. Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208. Grinderman, K. D.; Holtmann, P. Angew. Chem., Int. Ed. Engl. 1966, 7, 668. Verboom, W.; Meijer, J.; Brandsma, L. Synthesis 1978, 577.
3. Nazarov, N. I.; Zaretskaya, I.I. Zh. Obshch. Khim. 1957, 27, 693. Woodward, R. B.; Hoffmann, R. “The Conservation of Orbital Symmetry”; Verlag Chemie: Weinheim/Bergstr, Germany, 1970. Sorenson, T. S. J. Am. Chem. Soc. 1967, 89, 3784. Deno, N. C.; Pittman, C. V.; Turner, J. O. J. Am. Chem. Soc. 1965, 87, 2153. Ohloff, G.; Schulte, K. H.; Demole, E. Helv. Chim. Acta 1971, 54, 2813. For a recent example of a silicon-directed Nazarov cyclization see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
4. For leading references to the electrophilic chemistry of vinylsilanes see: ref 1. Fleming, I.; Pearce, A., J. Chem. Soc., Chem.Commun. 1975, 633. Chan, T. H.; Lau, P. W. K.; Mychajlowskij Tetrahedron Lett. 1977, 3317. Fristad, W. E.; Dime, D. S.; Bailey, T. R.; Paquette, L. A. Tetrahedron Lett. 1979, 1999; J. Org. Chem. 1980, 45, 3017. Hudrlick, P. F.; Hudrlick, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993. (5) For a leading and authoritative description of the synthetic chemistry of vinylsulfides see: Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075 and references therein. Hopskins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208. Oshima, K.; Shimojii, K.; Takashi, H.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1973, 95, 2694. Vlattas, I.; Veechia, L. D.; Lee, A. D. J. Am. Chem. Soc. 1976, 98, 2008. Cookson, R. C.; Parsons, P. J. J. Chem. Soc, Chem. Commun. 1976, 990. Cohen, T.; Mura, A. J.; Skull, D. W.; Fogel, E. R.; Ruffner, R. J.; Falck, J. R. J. Org. Chem. 1976, 41, 3218. Trost, B. M.; Crimmin, M. J.; Butler, D. J. Org. Chem. 1978, 43, 4549. Harirchian, B.; Magnus, P. J. Chem. Soc., Chem. Commun. 1977, 522. Posner, G. H.; Tang, P.-W. J. Org. Chem. 1978, 43, 4131.
5. For a preliminary account of this work see: Magnus, P.; Quagliato, D. A.; Huffman, J. C. Organometallics 1982, 1, 1240. Magnus, P.; Quagliato, D. A. Organometallics 1982, 1, 1243. (7) Cooke, F.; Moerck, R.; Schwinderman, J.; Magnus, P. J. Org. Chem. 1980, 45, 1046. (a) Ager, D. Tetrahedron Lett. 1982, 23, 1945. Hase, T. A.; Lahtinen, L. Tetrahedron Lett. 1981, 22, 3285. (8) Komarov, N. V.; Torosh, O. G., Izv. Akad. Nauk SSR Ser. Khim. 1967, 3, 690.
6. Gerber, U.; Widmer, U.; Schmid, R. Helv. Chim. Acta 1978, 83, 61. Kozikowski, A. P.; Huie, E.; Springer, J. P. J. Am. Chem. Soc. 1982, 104, 2059 and reference cited therein. Browbridge, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1976, 2125.
7. The isolation, structure, and first synthesis of hirsutene was reported by Nozoe in 1976: Nozoe, S.; Furukawa, J.; Sankawa, U.; Shibata, S. Tetrahedron Lett. 1976, 195. Ohfune, Y.; Shirahama, H.; Matsumoto, T., Tetrahedron Lett. 1978, 1991. Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. Greene, A. E. Tetrahedron Lett 1980, 3059. Hudlicky, T.; Kutchan, T.; Wilson, S. R.; Mao, D. T. J. Am. Chem. Soc. 1980, 102, 6351. Little, R. D.; Muller, G. W. J. Am. Chem. Soc. 1981, 103, 2744. Mehta, G.; Reddy, A. V. J. Chem. Soc., Chem. Commun. 1981, 756. Wender, P. A.; Howbert, J. J. Tetrahedron Lett. 1982, 3983. Hayano, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. Helv. Chim. Acta 1981, 64, 1347. Ley, S. V.; Murray, P. J. J. Chem. Soc., Chem. Commun. 1982, 1252. Little, R. D.; Higby, R. G.; Moeller, K. D. J. Org. Chem. 1983, 48, 3139. Dawson, B. A.; Ghosh, A. K.; Jurlina, J. L.; Stothers, J. B. J. Chem. Soc., Chem. Commun. 1983, 204.
8. For a recent review of polyquinane chemistry see: Paquette, L. A. “Recent Synthetic Developments in Polyquinane Chemistry”; Springer-Verlag: Berlin, 1984.
9. Capiano, L.; Kirn, R. H.; Zander, R. Chem. Ber. 1976, 109, 2456. Froberg, J.; Magnusson, G. J. Am. Chem. Soc. 1978, 100, 6728. (14) 4,7,7-Trimethyl-cis-bicyclo[3.3.0]oct-3-en-2-one is a well-known compound that has been prepared by a variety of routes: Fex, T.; Froberg, J.; Magnusson, G.; Thoren, S. J. Org. Chem. 1976, 41, 3518. (This is a very convenient method, especially on a large scale.) Ohfune, Y.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1975, 4377. Miyano, K.; Ohfune Y.; Azuma, S.; Matsumoto, T. Tetrahedron Lett. 1974, 1545. Paquette, L.; Farkas, E.; Galemmo, R. J. Org. Chem. 1981, 46, 5434.
10. Semmelhack, M. F.; Yamashita, A.; Tomesch, J. C.; Hirotsu, K. J. Am. Chem. Soc. 1978, 100, 5565.
11. Piers, E.; Karunaratne, V. J. Chem. Soc., Chem. Commun. 1983, 935. (17) Boeckman, R. K., Jr.; Blum, D. M. J. Org. Chem. 1974, 39, 3307.
12. Seebach, D.; Newman, H. Ber. Dtsch. Chem. Ges. 1974, 107, 847.
13. Suzuki, M.; Suzuki, T.; Kawagishi, T.; Noyori, R. Tetrahedron Lett. 1980, 1247. Hooz, J.; Layton, R. B. Can. J. Chem. 1970, 48, 1626.
14. Smith, A. B.; Jerris, P. J. Am. Chem. Soc. 1981, 103, 194.
15. Carpino, L. A. J. Chem. Soc., Chem. Commun. 1979, 514. (22) Hayano, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. Helv. Chim. Acta 1981, 64(5), 1347.
16. Barton, D. H. R.; Motherwell, W. B.; Stange, A. Synthesis 1981, 743.
17. Barton, D. H. R.; Motherwell, W. B. Pure Appl. Chem. 1981, 53, 15 and references therein. Barton, D. H. R.; McCombis, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
18. McElvain, S. M.; Starn, R. E., Jr. J. Am. Chem. Soc. 1955, 77, 4571. Dev, S. J. Indian Chem. Soc. 1956, 33, 11. Bosshard, H. H.; Mory, R.; Schmid, M.; Zollinger, H. Helv. Chim. Acta 1959, 42, 1653. (26) Doering, W. von E.; Depuy, C. H. J. Am. Chem. Soc. 1953, 75, 5955. Capiano, L.; Kirn, R. H.; Zander, R. Chem. Ber. 1976, 109, 2456.