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Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation.

ABSTRACT: Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of desired product to deformylated product.

SUBMITTER: Kim P

PROVIDER: S-EPMC1450324 | biostudies-literature | 2006 May

REPOSITORIES: biostudies-literature

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Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation.

Kim Pilho P Barry Clifton E CE Dowd Cynthia S CS

Tetrahedron letters 20060501 20

Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of desired product to deformylated product. ...[more]

PMID: 16699591

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