A Total Synthesis of FK-5061

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 α-allyl aldol functionality is revealed by a reductive...

Full description

Saved in:
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
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
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 α-allyl aldol functionality is revealed by a reductive opening of the spiroenone system. The labile α,β-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:0022-3263
1520-6904
DOI:10.1021/jo951646q