Journal
CANADIAN JOURNAL OF CHEMISTRY
Volume 82, Issue 2, Pages 353-365Publisher
CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS
DOI: 10.1139/V03-199
Keywords
pateamine A; immunosuppressive agent from marine sponge Mycale sp; total synthesis; novel 19-membered bis-lactone; thiazole metabolite; polyenamine; Stille reaction; sulfinimines; chiral beta-amino esters
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A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (1) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp(2)-sp(2) coupling reaction to elaborate the E,Z-diene macrolide core 23 and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral beta-amino ester moieties in complex structures.
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