Journal of Organic Chemistry 2001-11-02

Total synthesis of (+/-)-asteriscanolide.

M E Krafft, Y Y Cheung, K A Abboud

Index: J. Org. Chem. 66(22) , 7443-8, (2001)

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Abstract

The total synthesis of asteriscanolide (1) has been achieved by taking advantage on an intermolecular Pauson-Khand cycloaddition and a ring-closing metathesis as key bond-forming transformations. The approach incorporates the cyclooctane stereogenic center prior to ring formation. Interestingly, the ring-closing metathesis generates a new eight-membered ring with an "in-out" intrabridgehead relationship.