Journal
TETRAHEDRON
Volume 66, Issue 1, Pages 187-196Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.10.115
Keywords
Aldol; Butenolide; Dithiane; Ring-closing metathesis; Stereochemistry
Categories
Funding
- Research Grants Council [600808]
- The Hong Kong Special Administrative Region, China
- Department of Chemistry, HKUST
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Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.
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