Asymmetric synthesis of seven-carbon segments of the phorboxazoles and (−)-discodermolide: Complementary route from racemic trans-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

The C20–C26 segment of the phorboxazoles A and B and the C1–C7 segment of (−)-discodermolide were synthesized in excellent chemical and optical yield using trans-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one rac-1 with four stereogenic centres and three prostereogenic sp 2-sites as an early racemic...

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Bibliographic Details
Published inTetrahedron Vol. 55; no. 14; pp. 4315 - 4324
Main Authors Misske, Andrea M, Hoffmann, H.M.R
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.04.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
SPONGE PHORBAS SP
ABSOLUTE-CONFIGURATION
DISCODERMOLIDE
NATURAL-PRODUCTS
ALKYLATION
FRAGMENT
C-21 SECTOR
STEREOSELECTIVE SYNTHESIS
MARINE SPONGE
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Summary:The C20–C26 segment of the phorboxazoles A and B and the C1–C7 segment of (−)-discodermolide were synthesized in excellent chemical and optical yield using trans-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one rac-1 with four stereogenic centres and three prostereogenic sp 2-sites as an early racemic switch. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00127-1