A total synthesis of (+)-Goniodiol using an anomeric oxygen-to-carbon rearrangement

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 19, 1998, Pages 3125-3126

  Dixon, Darren J ^a   Ley, Steven V ^a   Tate, Edward W ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749115510     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806584e     Document Type: Article

References (18)

1. B. Talapatra, S. K. Talapatra, D. Basu, T. Deb and S. Goswami, Indian J. Chem., Sect. B, 1985, 24, 29.
2. X.-P. Fang, J. E. Anderson, C.-J. Chang, J. L. McLaughlin and P. E. Fanwick, J. Nat. Prod., 1991, 54, 1034.
3. For example, Y.-C. Wu, C.-Y. Duh, F.-R. Chang, G.-Y. Chang, S.-K. Wang, J.-J. Chang, D. R. McPhail, A. T. McPhail and K.-H. Lee, J. Nat. Prod., 1991, 54, 1077.
4. (a) M. F. Buffet, D. J. Dixon, G. L. Edwards, S. V. Ley and E. W. Tate, Synlett, 1997, 1055;
5. (b) M. F. Buffet, D. J. Dixon, S. V. Ley and E. W. Tate, Synlett, in press;
6. (c) D. J. Dixon, S. V. Ley and E. W. Tate, Synlett, in press.
7. For previous total syntheses of this molecule, see (a) M. Tsubuki, K. Kanai and T. Honda, J. Chem. Soc., Chem. Commun., 1992, 1640;
8. (b) J.-P. Surivet, J. Goré and J.-M. Vatèle, Tetrahedron Lett., 1996, 37, 371;
9. (c) C. Mukai, S. Hirai and M. Hanaoka, J. Org. Chem., 1997, 62, 6619.
10. R. J. K. Taylor, Organocopper Reagents, Oxford University Press, Oxford, 1994, and references cited therein.
11. Direct treatment of the lactol 3 with α-bromoacetophenone in the presence of a variety of bases gave extensive decomposition of the starting material.
12. S. M. Weinreb and S. Nahm, Tetrahedron Lett., 1981, 22, 3815.
13. The configuration of the silyl enol ether was tentatively assigned by analogy with previous work.
14. 3Si).
15. S. L. Huang, K. Omura and D. Swern, Synthesis, 1978, 297.
16. For example: J. E. Baldwin, A. K. Forrest, S. Ko and L. N. Sheppard, J. Chem. Soc., Chem. Commun., 1987, 81.
17. L. S. Jeong, R. F. Schinazi, J. W. Beach, H. O. Kim, S. Nampalli, K. Shanmuganathan, A. J. Alves, A. McMillan, C. K. Chu and R. Mathis, J. Med. Chem., 1993, 36, 181.
18. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639.