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Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers

Yang, F and Newsome, JJ and Curran, DP (2006) Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers. Journal of the American Chemical Society, 128 (43). 14200 - 14205. ISSN 0002-7863

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Abstract

Techniques of fluorous mixture synthesis have been used to make four candidate stereoisomers for the natural product lagunapyrone B. A quasiracemic mixture of vinyl iodides whose component configurations at C19-21 were encoded by fluorous silyl groups was fused to a central fragment by a Negishi coupling. A separate quasiracemic mixture of pyrone fragments whose component configurations at C6,7 were also encoded by fluorous silyl groups was synthesized and demixed. Stille coupling of the resulting pure quasienantiomers with the quasiracemic mixture provided two quasi-diastereomeric samples, which were demixed and detagged to provide all four lagunapyrone B stereoisomers. Lagunapyrone was assigned the 6R,7S,19S,20S,21R configuration by comparison of optical rotations. © 2006 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Yang, F
Newsome, JJ
Curran, DPcurran@pitt.eduCURRAN
Date: 1 November 2006
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 128
Number: 43
Page Range: 14200 - 14205
DOI or Unique Handle: 10.1021/ja064812s
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Alkenes--chemistry; Molecular Structure; Pyrones--chemistry; Stereoisomerism
PubMed ID: 17061905
Date Deposited: 28 May 2013 15:16
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/18738

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