A Total Synthesis of FK-506(1)

A total synthesis of FK-506 (1) is presented. The synthesis features a highly convergent approach utilizing a block coupling strategy. Top and bottom half sections of the molecule are coupled by addition of a vinyl cuprate with a spiroenone. The alpha-allyl aldol functionality is revealed by a reduc...

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Bibliographic Details
Published in:Journal of organic chemistry 1996-10, Vol.61 (20), p.6856-6872
Main Authors: Ireland, Robert E., Gleason, James L., Gegnas, Laura D., Highsmith, Thomas K.
Format: Article
Language:English
Online Access:Get full text
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Summary:A total synthesis of FK-506 (1) is presented. The synthesis features a highly convergent approach utilizing a block coupling strategy. Top and bottom half sections of the molecule are coupled by addition of a vinyl cuprate with a spiroenone. The alpha-allyl aldol functionality is revealed by a reductive opening of the spiroenone system. The labile alpha,beta-diketoamide hemiketal portion of the molecule is prepared by a late stage generation and oxidation of a masked enediol. Top and bottom half segments are themselves derived by coupling of smaller subunits, resulting in a very convergent route.
ISSN:1520-6904
DOI:10.1021/jo951646q