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Total synthesis of (+)-SCH 351448.

Authors
  • Zhu, Kaicheng
  • Panek, James S
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Sep 02, 2011
Volume
13
Issue
17
Pages
4652–4655
Identifiers
DOI: 10.1021/ol201863b
PMID: 21834568
Source
Medline
License
Unknown

Abstract

A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C(2)-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide.

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