Studies on the total synthesis of the macrolide antitumor agent rhizoxin. 1. Synthesis of the C3C13 segment

An asymmetric synthesis of the C3C13 segment of rhizoxin is described in which the relative stereochemistry of C7 and C8 is established through a chelation-controlled allylation followed by Mitsunobu inversion, and the pyran ring is constructed by a photochemically initiated 6- exo radical cyclizat...

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Bibliographic Details
Published in:Tetrahedron letters 1997-10, Vol.38 (42), p.7329-7332
Main Authors: White, James D., Nylund, Christine S., Green, Neal J.
Format: Article
Language:English
Subjects:
nonfood plant products
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Summary:An asymmetric synthesis of the C3C13 segment of rhizoxin is described in which the relative stereochemistry of C7 and C8 is established through a chelation-controlled allylation followed by Mitsunobu inversion, and the pyran ring is constructed by a photochemically initiated 6- exo radical cyclization. Synthesis of a segment representing C3C13 of rhizoxin was completed using radical cyclization of an iodo α,β-unsaturated nitrile to construct the pyran subnit.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01780-2