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Synthesis of the C22−C26 Tetrahydropyran Segment of Phorboxazole by a Stereoselective Prins Cyclization

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posted on 2000-04-12, 00:00 authored by Scott D. Rychnovsky, Christian R. Thomas
Tetrahydropyran rings are found in many complex natural products, and the segment-coupling Prins cyclization is an effective strategy for their synthesis. We report a four-step, stereoselective synthesis of the C20−C27 tetrahydropyran segment of phorboxazole. The key step is a Prins cyclization induced by catalytic BF3·OEt2.

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