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Stereocontrolled Synthesis of the Northern Part of Potent Proteasome Inhibitor TMC-95A

A protected version of the northern part of TMC-95A, a potent and selective proteasome inhibitor, was synthesized with full stereochemical control. Highlights of this synthesis include (i) a (Z)-selective Mizoroki−Heck reaction to construct the oxyindole portion, (ii) a diastereoselective epoxidatio...

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Bibliographic Details
Published in:Organic letters 2001-09, Vol.3 (18), p.2863-2865
Main Authors: Inoue, Masayuki, Furuyama, Hidetomo, Sakazaki, Hayato, Hirama, Masahiro
Format: Article
Language:English
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Summary:A protected version of the northern part of TMC-95A, a potent and selective proteasome inhibitor, was synthesized with full stereochemical control. Highlights of this synthesis include (i) a (Z)-selective Mizoroki−Heck reaction to construct the oxyindole portion, (ii) a diastereoselective epoxidation, (iii) a 6-endo selective epoxide opening by Boc carbonyl group to establish the stereochemistry of C6, and (iv) a 1,3-elimination reaction of the l-allo-threonine derivative under Mitsunobu conditions to afford the (Z)-1-propenylamine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016303v