Studies on the total synthesis of the macrolide antitumor agent rhizoxin. 2. Synthesis of the C14C26 segment

An asymmetric synthesis of the C14C26 segment of rhizoxin is described in which the three stereogenic centers are derived from a γ-lactone; stannylcupration-methylation of a terminal alkyne is used to generate an ( E)-iodoalkene for Stille coupling with a dienylstannane that produces the conjugated...

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Bibliographic Details
Published in:Tetrahedron letters 1997-10, Vol.38 (42), p.7333-7336
Main Authors: White, James D., Holoboski, Mark A., Green, Neal J.
Format: Article
Language:English
Subjects:
nonfood plant products
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Summary:An asymmetric synthesis of the C14C26 segment of rhizoxin is described in which the three stereogenic centers are derived from a γ-lactone; stannylcupration-methylation of a terminal alkyne is used to generate an ( E)-iodoalkene for Stille coupling with a dienylstannane that produces the conjugated ( E, E, E)-triene unit of rhizoxin. The C14C26 subunit of rhizoxin was synthesized via Stille coupling of a known dienylstannane with an ( E)-iodoalkene, prepared via stannylcupration-iodination of an alkyne originating in D-glutamic acid.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01781-4