Total synthesis of formamicin

Academic Article

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Overview

authors

• Durham, T. B.
• Blanchard, N.
• Savall, B. M.
• Powell, N. A.
• Roush, William

publication date

• 2004

journal

• Journal of the American Chemical Society  Journal

abstract

• The enantioselective total synthesis of the cytotoxic plecomacrolide natural product formamicin (1) is described. Key aspects of this synthesis include the efficient transacetalation reactions of MOM ethers 28 and 38 to form the seven-membered formyl acetals 29 and 39, a late-stage Suzuki cross-coupling reaction of the highly functionalized vinyl boronic acid 6 and vinyl iodide 7, a highly beta-selective glycosidation reaction of beta-hydroxy ketone 4 with 2,6-dideoxy-2-iodoglucopyranosyl fluoride 3, and the global desilylation of penultimate intermediate 77 mediated by in situ generated Et(3)N.2HF.

subject areas

• Glycosylation
• Macrolides
• Stereoisomerism

Identity

International Standard Serial Number (ISSN)

• 0002-7863

Digital Object Identifier (DOI)

• 10.1021/ja048493i

PubMed ID

• 15281821

Additional Document Info

start page

• 9307

end page

• 9317

volume

• 126

issue

• 30