C O M M U N I C A T I O N S
Scheme 2
Scheme 5
Acknowledgment. Financial support was provided by the
American Cancer Society (RSG-04-017-CDD). A.V.S. acknowl-
edges the support of Burroughs Wellcome Fund Interfaces No.
1001774. S.A.K. is a fellow of the Alfred P. Sloan Foundation.
S.A.K. thanks the Dreyfus Foundation for a Teacher-Scholar Award
and Amgen, Inc. for a New Investigator Award. We thank Professor
G. F. Biard for a generous sample of bistramide A.
Scheme 3
Supporting Information Available: Full characterization of new
compounds and selected experimental procedures. This information is
References
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J. F. J. Nat. Prod. 1994, 57, 1336.
Scheme 4
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(17) Stereochemical outcome of C-glycosidation is consistent with the axial
delivery of enol silane to the oxonium ion intermediate having the
pseudoequatorial siloxyethyl and axial methyl substituents.
13C NMR, HPLC, optical rotation) with the natural sample of
bistramide A.
In closing, we have developed a highly convergent, fully
diastereocontrolled and efficient synthesis of bistramide A, which
provided unambiguous structural assignment of this complex natural
product and set the stage for the detailed investigation of its
chemical biology. Our approach featured a novel and potentially
broadly applicable olefin metathesis-based strategy for the spiroketal
construction.
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