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Synthesis 2010(4): 631-642
DOI: 10.1055/s-0029-1218608
DOI: 10.1055/s-0029-1218608
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthetic Studies on the Sporolides: Exploration of the Enediyne Route
Further Information
Received
10 September 2009
Publication Date:
16 December 2009 (online)
Publication History
Publication Date:
16 December 2009 (online)
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Abstract
Synthetic studies towards the construction of the cyclopenta[a]indene fragment of the heptacyclic marine metabolite sporolide are reported based on a hypothetical biosynthesis. The key step of this biogenetic proposal includes a Bergman cyclization of an enediyne precursor. The enediyne target of this synthetic study was prepared by Sonogashira cross-coupling of two fragments, of which the cyclopentane fragment was prepared from cyclopentenone, Morita-Baylis-Hillman reaction, and enantioselective Sharpless dihydroxylation.
Key words
cross-coupling - natural products - oxidations - stereoselective synthesis - total synthesis
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