Synthetic studies on the rhizoxins. II. An approach to the C10-C26 subunit using "substrate directed" allylstannane additions to aldehydes

Gary E. Keck; Kenneth A. Savin; Michael A. Weglarz; Erik N.K. Cressman

doi:10.1016/0040-4039(96)00578-3

Synthetic studies on the rhizoxins. II. An approach to the C₁₀-C₂₆ subunit using "substrate directed" allylstannane additions to aldehydes

Gary E. Keck, Kenneth A. Savin, Michael A. Weglarz, Erik N.K. Cressman

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

The construction of a C₁₀-C₂₆ fragment of the 16-membered antitumor macrolide rhizoxin has been achieved in an efficient manner. The central portion of this molecule has been prepared in enantiopure form via an iterative allylstannylation protocol starting with the ester of (R)-lactic acid. The oxazole portion of rhizoxin was attached via a samarium diiodide modified Julia coupling to generate the requisite all E triene.

Original language	English (US)
Pages (from-to)	3291-3294
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	19
DOIs	https://doi.org/10.1016/0040-4039(96)00578-3
State	Published - May 6 1996
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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AU - Weglarz, Michael A.

AU - Cressman, Erik N.K.

PY - 1996/5/6

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AB - The construction of a C10-C26 fragment of the 16-membered antitumor macrolide rhizoxin has been achieved in an efficient manner. The central portion of this molecule has been prepared in enantiopure form via an iterative allylstannylation protocol starting with the ester of (R)-lactic acid. The oxazole portion of rhizoxin was attached via a samarium diiodide modified Julia coupling to generate the requisite all E triene.

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Synthetic studies on the rhizoxins. II. An approach to the C₁₀-C₂₆ subunit using "substrate directed" allylstannane additions to aldehydes

Abstract

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