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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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Published in: | Organic letters 2001-09, Vol.3 (18), p.2863-2865 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol016303v |