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2000•Organic LettersRequires access

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

Scott D. Rychnovsky, Christian R. Thomas

Open publisher page 118 citations

Abstract

[formula: see text] 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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What this paper is about

[formula: see text] 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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Available abstract

[formula: see text] 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.

Key concepts: Tetrahydropyran, Prins reaction, Stereoselectivity, Chemistry, Stereochemistry, Combinatorial chemistry, Catalysis, Organic chemistry

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Synthesis of the C22−C26 Tetrahydropyran Segment of Phorboxazole by a Stereoselective Prins Cyclization — Research Paper | ScholarLens