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Total Synthesis of (±)-Asteriscanolide

2001; American Chemical Society; Volume: 66; Issue: 22 Linguagem: Inglês

10.1021/jo010623a

1520-6904

Marie E. Krafft, Yiu‐Yin Cheung, Khalil A. Abboud,

Marine Toxins and Detection Methods

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.