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Synthesis 1995; 1995(9): 1097-1101
DOI: 10.1055/s-1995-4061
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A Predictable Enantioselective Total Synthesis of (+)-Clavularin A

Hilmar Weinmann, Ekkehard Winterfeldt*
  • *Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany, Fax +49(511)7623011; E-mail Winterfeldt@mbox.OCI.UNI-HANNOVER.DE
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Publication Date:
31 December 2000 (online)

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Cycloadduct 9 was transformed into vinylsilane 11d in a conjugate addition-alkylation sequence. Epoxidation and subsequent hydrolysis provided the clavularin adduct 14, which on flash vacuum pyrolysis (FVP) gave (+)-clavularin A (1) in 91% yield.

diene synthesis - cycloheptenone adducts - cuprate addition - diastereoselective alkylations - retro-Diels-Alder reaction

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