Enantioselective synthesis of medium-ring sub-units of brevetoxin A by ring-closing metathesis

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 127-130

  Clark, J Stephen ^a   Kettle, Jason G ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BREVETOXIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0031023477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02233-2     Document Type: Article

References (18)

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2. Shimizu, Y.; Chou. H.-N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Am. Chem. Soc., 1986, 108, 514. Pawlak, J.; Tempesta, M. S.; Golik, J.; Zagorski, M. G.; Lee, M. S.; Nakanishi, K.; Iwashita, T.; Gross, M. L.; Tomer, K. B. J. Am. Chem. Soc., 1987, 109, 1144. Zagorski, M. G.; Nakanishi, K.: Qin, G.; Lee, M. S. J. Org. Chem., 1988, 53, 4156.
3. Shimizu, Y.; Chou. H.-N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Am. Chem. Soc., 1986, 108, 514. Pawlak, J.; Tempesta, M. S.; Golik, J.; Zagorski, M. G.; Lee, M. S.; Nakanishi, K.; Iwashita, T.; Gross, M. L.; Tomer, K. B. J. Am. Chem. Soc., 1987, 109, 1144. Zagorski, M. G.; Nakanishi, K.: Qin, G.; Lee, M. S. J. Org. Chem., 1988, 53, 4156.
4. For a recent review of marine toxins, see: Yasumoto, T.; Murata, M. Chem. Rev., 1993, 93, 1897.
5. For some examples of previous efforts to construct medium-ring sub-units of brevetoxin A, see: Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc., 1990, 112, 3696. Nicolaou, K. C.: Prasad, C. V. C.; Ogilvie, W. W. J. Am. Chem. Soc.. 1990,112, 4988. Nicolaou, K. C.; Veale, C.A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W. Angew. Chem. Int. Ed. Engl., 1991, 30, 299.
6. For some examples of previous efforts to construct medium-ring sub-units of brevetoxin A, see: Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc., 1990, 112, 3696. Nicolaou, K. C.: Prasad, C. V. C.; Ogilvie, W. W. J. Am. Chem. Soc.. 1990,112, 4988. Nicolaou, K. C.; Veale, C.A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W. Angew. Chem. Int. Ed. Engl., 1991, 30, 299.
7. For some examples of previous efforts to construct medium-ring sub-units of brevetoxin A, see: Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc., 1990, 112, 3696. Nicolaou, K. C.: Prasad, C. V. C.; Ogilvie, W. W. J. Am. Chem. Soc.. 1990,112, 4988. Nicolaou, K. C.; Veale, C.A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W. Angew. Chem. Int. Ed. Engl., 1991, 30, 299.
8. Clark, J. S.; Kettle, J. G. Tetrahedron Lett., preceding publication in this issue.
9. The catalyst (1) used in these studies was purchased from Strem Chemicals U.K.
10. Fu, G. C.: Grubbs, R. H. J. Am. Chem. Soc., 1992. 114. 5426. Fu, G. C.; Nguyen S. T.; Grubbs, R. H. J. Am. Chem. Soc., 1993, 115, 9856.
11. Fu, G. C.: Grubbs, R. H. J. Am. Chem. Soc., 1992. 114. 5426. Fu, G. C.; Nguyen S. T.; Grubbs, R. H. J. Am. Chem. Soc., 1993, 115, 9856.
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13. 2.
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17. The minor epimers of 9 and 10 were separated after conversion of these compounds into the p-methoxybenzylidene acetals 11 and 12 (Scheme 2).
18. A similar stereochemical dependency of yield has been observed when attempting to construct fused eight-membered rings by ring-closing metathesis: Miller, S. J.; Kim, S.-H.: Chen, Z.-R. and Grubbs, R. H. J. Am. Chem. Soc., 1995, 777, 2108.