rings with 7 or more members rings with 7 or more members Q 0050 -085Radical Cation-Mediated Annulation. Stereoselective Construction of Bicyclo[5.3.0]decan-3-ones by Aerobic Oxidation of Cyclopropylamines.-Intramolecular Kulinkovich cyclopropanation of olefin-tethered amides such as (I) and (VII) followed by tandem ring expansion-cyclization of the resulting bicyclic aminocyclopropenes offers a stereocontrolled method to prepare bicyclo[5.3.0]decan-3-ones.

Starting with the tricyclic core 2b, annulation to form the 13-membered western ring of sarain A has been achieved to afford the macrocycle 30a by initial construction of the sterically congested quaternary center at C-3, followed by elaboration of the C-3 side-chain and ring-closing olefin metathesis. Also included is a parallel conversion of tricycle 2c to macrocycle 30b containing a functionalized side-chain at N-1 suitable for attachment of the eastern macrocyclic ring.

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