An Unusual Substituent Effect on a Palladium-Mediated Cyclization: A Total Synthesis of (±)-Sterepolide

Journal of the American Chemical Society

Volumn 107, Issue 15, 1985, Pages 4586-4588

  Trost, Barry M ^a   Chung, John Y L ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845379681     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00301a056     Document Type: Article

References (11)

1. (1) For a review, see: Ayer, W. A.; Browne, L. M. Tetrahedron 1981, 37, 2199.
2. (2) (a) Isolactarorufin: Daniewski, W. M.; Kocor, M.; Thoren, S. Pol. J. Chem. 1978, 52, 561. Konitz, A.; Bogucka-Ledochowska, M.; Dautker, Z.; Hempel, A.; Borowski, E. Tetrahedron Lett. 1977, 3401. (b) Sterepolide and dihydrosterepolide: Ayer, W. A.; Saeedi-Ghomi, M. H. Tetrahedron Lett. 1981, 22, 2071. (c) Merulidial: Steglich, W. Pure Appl. Chem. 1981, 53, 1233.
3. Boeckman, (3) Cf. the elegant marasmic acid synthesis: Greenlee, W. J.; Woodward, R. B. J. Am. Chem. Soc. 1976, 98, 6075. Tetrahedron, 1980, 36, 3367; R. K. Jr.; Ko, S. S. J. Am. Chem. Soc. 1980, 102, 7146.
4. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781.
5. (5) (a) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265. (b) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. (c) Tamaru, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron 1979, 35, 329. (6) Hirao, T.; Enda, J.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1981, 403.
6. (7) For the corresponding THP ether, see: Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1975, 40, 2265.
7. (8) Ho, T.-L.; Wong, C. M. Synth. Commun. 1974, 4, 147. Stevens, R. V.; Christensen, C. G.; Edmonson, W. L.; Kaplan, M.; Reid, E. B.; Wentland, M. P. J. Am. Chem. Soc. 1971, 93, 6629.
8. (9) Cf.: Stephenson, T. A.; Morehouse, S. M.; Powell, A. R.; Heffer, J. P.; Wilkinson, G. J. Chem. Soc. 1965, 3632.
9. (10) Kuwajima, I.; Nakamura, E. J. Am. Chem. Soc. 1975, 97, 3257.
10. (11) Brown, H. C.; Bigley, D. B. J. Am. Chem. Soc. 1961, 83, 486.
11. (12) Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.