Oxepanes from an unusual acetal cleavage of 6,8-dioxabicyclo[3.2.1]octanes

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 339-342

  Rychnovsky, Scott D ^a,b   Dahanukar, Vilas H ^a  

^a University of Minnesota   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

acetal cleavage; brevetoxin; reductive decyanation; TMSCN

Indexed keywords

OXEPANE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030045514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02167-1     Document Type: Article

References (13)

1. Fotsch, C. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4141.
2. MacroModel V4.5: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
3. A group of conformers was identified using a Monte Carlo search, and the coupling constants were calculated using the coplf function, which evaluates a Boltzmann weighted average at 25 °C. Haasnoot, C. A. G.; DeLeeuw, F. A. A. M.; Altona, C. Tetrahedron, 1980, 36, 2783.
4. The epoxy ketones were prepared by the following route: (equation presented)
5. 3Al did not react with bicyclic acetal 2.
6. Synthesis of brevetoxin B: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao X.-Y. J. Am. Chem. Soc. 1995, 117, 1171.
7. (b) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller E. J. Am. Chem. Soc. 1995, 117, 1173.
8. Rychnovsky, S. D.; Zeller, S.; Skalitzky, D. J.; Griesgraber, G. J. Org. Chem. 1990, 55, 5550.
9. Reduction of 5,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane with alane gave a cis-tetrahydropyran: Kim, Y.; Mundy, B. P. J. Org. Chem. 1982, 47, 3556. See also Kotsuki, H. Synlett 1992, 97.
10. Reduction of 5,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane with alane gave a cis-tetrahydropyran: Kim, Y.; Mundy, B. P. J. Org. Chem. 1982, 47, 3556. See also Kotsuki, H. Synlett 1992, 97.
11. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
12. Mulholland, R. L.; Chamberlin, A. R. J. Org. Chem. 1988, 53, 1082.
13. Support for this work was provided by the Eli Lilly Grantee program and the Alfred P. Sloan Foundation.