Literature DB >> 11405688

Formal [4+2]-annulation of chiral crotylsilanes: synthesis of the C19-C28 fragment of phorboxazoles.

H Huang1, J S Panek.   

Abstract

A stereoselective synthesis of the C19-C28 fragment of phoborxazole A and B is described. The key step is an enantioselective [4 + 2]-annulation of a crotylsilane 10 with a propargylic aldehyde 11 affording a functionalized dihydropyran 12. A solvent-dependent stereoselective epoxidation of dihydropyrans is also documented.

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Year:  2001        PMID: 11405688     DOI: 10.1021/ol015893u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

Review 1.  Synthesis of the phorboxazoles-potent, architecturally novel marine natural products.

Authors:  Zachary Shultz; James W Leahy
Journal:  J Antibiot (Tokyo)       Date:  2016-03-09       Impact factor: 2.649

2.  Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes.

Authors:  Barry M Trost; Dennis C Koester; Ehesan U Sharif
Journal:  Chemistry       Date:  2016-01-25       Impact factor: 5.236

  2 in total

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