Asymmetric Synthesis of Calyculin C. 2. Synthesis of the C26−C37 Fragment and Model Wittig Couplings
The Journal of Organic Chemistry1996Vol. 61(18), pp. 6153–6161
Citations Over TimeTop 10% of 1996 papers
Anthony K. Ogawa, John A. DeMattei, Gerard R. Scarlato, John E. Tellew, Lee S. Chong, Robert W. Armstrong
Abstract
We report our synthesis of the C(26)-C(37) fragment of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C (1). Outlined in this paper are synthetic approaches to the two components based on disconnection at the C(33)-N(3) amide bond. We report the successful synthesis of the C(33)-C(37) aza-sugar derived from D-lyxose which was coupled onto a C(26)-C(32) aminooxazole originating from L-pyroglutamic acid. Elaboration of the resulting amide to a fully deprotected C(26)-C(37) fragment of calyculin C completed our synthesis. This provided an appropriate phosphonium salt for use in a Wittig olefination for joining both halves of the natural product.
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