Studies on the synthesis of reidispongiolide A: stereoselective synthesis of the C(22)-C(36) fragment

A highly stereoselective synthesis of the C(22)-C(36) fragment 2 of reidispongiolide A is described. This synthesis features the highly stereoselective mismatched double asymmetric crotylboration reaction of the aldehyde derived from 5 and the new chiral reagent (S)-(E)-7 that provides 12 with >1...

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Bibliographic Details
Published inTetrahedron Vol. 67; no. 52; pp. 10274 - 10280
Main Authors Ying, Maben, Roush, William R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 30.12.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Mismatched double asymmetric crotylboration
HYDROBORATION
STEREOTRIAD
POTENT CYTOTOXIC MACROLIDES
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
Stereoselective synthesis of the anti,anti stereotriad
SIMPLIFIED ANALOGS
ALCOHOLS
SPHINXOLIDES
Studies on the synthesis of reidispongiolide A
REDUCTION
STEREOCHEMICAL ASSIGNMENT
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Summary:A highly stereoselective synthesis of the C(22)-C(36) fragment 2 of reidispongiolide A is described. This synthesis features the highly stereoselective mismatched double asymmetric crotylboration reaction of the aldehyde derived from 5 and the new chiral reagent (S)-(E)-7 that provides 12 with >15:1dr. Subsequent coupling of the derived vinyl iodide 3 with aldehyde 16 provided allylic alcohol 17, that was elaborated by three steps into the targeted reidispongiolide fragment 2. (C) 2011 Elsevier Ltd. All rights reserved.
Bibliography:NIH RePORTER
ISSN:0040-4020
DOI:10.1016/j.tet2011.10.029