Total synthesis of ()-pateamine, a novel polyene bis-macrolide with immunosuppressive activity from the sponge Mycale sp

A concise and convergent synthesis of the polyene thiazole-containing 19-membered bis-lactone ()-pateamine 1 is described. The synthesis features both the intra- and intermolecular Stille sp 2– sp 2 coupling reactions to elaborate the E,Z-diene macrolide core and the side-chain all- E polyene porti...

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Bibliographic Details
Published in:Tetrahedron letters 2000-09, Vol.41 (38), p.7367-7371
Main Authors: Remuiñán, Modesto J, Pattenden, Gerald
Format: Article
Language:English
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Summary:A concise and convergent synthesis of the polyene thiazole-containing 19-membered bis-lactone ()-pateamine 1 is described. The synthesis features both the intra- and intermolecular Stille sp 2– sp 2 coupling reactions to elaborate the E,Z-diene macrolide core and the side-chain all- E polyene portion of the natural product, and highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β -amino ester moieties in complex structures.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)01241-7