Journal
TETRAHEDRON LETTERS
Volume 51, Issue 35, Pages 4599-4601Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.06.006
Keywords
Bistramide; Bisatratene; Enol ethers; Spiroketal; Lactone; Julia-Kocienski reagents; Natural product synthesis
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Funding
- European Commission [LSHB-CT-2004-503467]
- Ministere de la Recherche et de la Technologie
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An efficient synthesis of the spirocyclic fragment 1 of bistramides is reported. An olefination reaction of lactone 4 with sulfone 5 gave the enol ether 3, which upon cyclization in acidic media provided the spiroketal ring system. This compound was then converted into the C19-C36 fragment of the bistramides via successive Julia-Kocienski and Horner-Emmons olefinations. (C) 2010 Elsevier Ltd. All rights reserved.
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