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Total synthesis of cochleamycin A
Thomas A Dineen1, William R Roush
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Organic Letters
|June 5, 2004
Abstract:
[reaction: see text] Cochleamycin A (1) was synthesized in 2.4% overall yield via a 23-step linear sequence starting from 3-butene-1-ol. Key features of the synthesis include the synthesis of (Z)-1,3-diene 21 via a Stille coupling of 4 and 5 and a transannular Diels-Alder reaction of macrocycle 26 to provide the complete carbon skeleton of 1.