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Synlett 2000; 2000(4): 529-531
DOI: 10.1055/s-2000-6562
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Synthesis of the AB-Ring of 9,11-Secosterols

Riina Aav* , Tõnis Kanger, Tõnis Pehk, Margus Lopp
  • *Tallinn Technical University, Department of Chemistry, Ehitajate tee 5, Tallinn 19086, Estonia; Fax 3 72 6 54 75 20; E-mail: riina@chemnet.ee
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Publication Date:
31 December 2000 (online)

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The first total synthesis of AB-ring system of an antiproliferative and cytotoxic 9,11-secosterol 1 is described. Enantiomerically pure (3S,5S,6S,10S)-3,6-diacetoxy-10-methylbicyclo[4.4.0]decan-9-one 8 (steroidal numeration) was prepared from (S)-Wieland-Miescher ketone.

diastereoselectivity - hydroborations - bicyclic compounds - sterols - total synthesis