Asymmetric Synthesis of Calyculin C. 1. Synthesis of the C1−C25 Fragment
The Journal of Organic Chemistry1996Vol. 61(18), pp. 6139–6152
Citations Over TimeTop 10% of 1996 papers
Gerard R. Scarlato, John A. DeMattei, Lee S. Chong, Anthony K. Ogawa, Mavis R. Lin, Robert W. Armstrong
Abstract
We report our synthesis of the C(1)-C(25) fragment of serine/threonine phosphatase PP1 and PP2A inhibitor, calyculin C. Synthetic efforts were directed initially toward the synthesis of a spiroketal core fragment (7), which culminated in completion of the bottom half of the natural product. The synthesis of fragment 7 and subsequent elaboration relied on an allylboration strategy for introduction of chirality. The C(1)-C(8) fragment representing the potentially unstable tetraene moiety was introduced as a separate entity.
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