ECB-ART-43162
Angew Chem Int Ed Engl
2014 Jan 13;533:757-60. doi: 10.1002/anie.201307835.
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Total synthesis of (-)-ophiodilactone A and (-)-ophiodilactone B.
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The first asymmetric total synthesis of (-)-ophiodilactone A and (-)-ophiodilactone B, isolated from the ophiuroid (Ophiocoma scolopendrina), is reported. The key features of the synthesis include the highly stereocontrolled construction of the structurally congested γ-lactone/δ-lactone skeleton through an asymmetric epoxidation, diastereoselective iodolactonization, and intramolecular epoxide-opening with a carboxylic acid, and biomimetic radical cyclization of ophiodilactone A to ophiodilactone B.
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