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. 2004 Apr 30;69(9):3154-7.
doi: 10.1021/jo049955g.

Total synthesis of the nonadjacently linked bis-tetrahydrofuran acetogenin bullatanocin (squamostatin C)

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Total synthesis of the nonadjacently linked bis-tetrahydrofuran acetogenin bullatanocin (squamostatin C)

Lei Zhu et al. J Org Chem. .

Abstract

The total synthesis of the nonadjacently linked bis-THF acetogenin bullatanocin (squamostatin C) is described. The synthetic strategy is a modular one based on three components, two mono-THF alkenes and a butenolide precursor, and the olefin cross-metathesis and Wittig olefination as the segment-coupling reactions. The synthesis confirms the structure of the natural product, and its convergent design makes it especially attractive for analogue synthesis.

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