Radical Cyclization in Heterocycle Synthesis. 12.1) Sulfanyl Radical Addition-Addition-Cyclization (SRAAC) of Unbranched Diynes and Its Application to the Synthesis of A-Ring Fragment of 1α, 25-Dihydroxyvitamin D3

Okiko MIYATA; Emi NAKAJIMA; Takeaki NAITO

doi:10.1248/cpb.49.213

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Radical Cyclization in Heterocycle Synthesis. 12.¹⁾ Sulfanyl Radical Addition-Addition-Cyclization (SRAAC) of Unbranched Diynes and Its Application to the Synthesis of A-Ring Fragment of 1α, 25-Dihydroxyvitamin D₃

Okiko MIYATA, Emi NAKAJIMA, Takeaki NAITO

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Keywords: sulfanyl radical, addition-addition-cyclization, diyne, alkylidenecyclopentane, alkylidenecyclohexane, vitamin D

JOURNAL FREE ACCESS

2001 Volume 49 Issue 2 Pages 213-224

DOI https://doi.org/10.1248/cpb.49.213

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Abstract

Sulfanyl radical addition-addition-cyclization (SRAAC) of unbranched diynes proceeded smoothly to give cyclized exo-olefins, while the sulfanyl radical addition-cyclization-addition (SRACA) of diynes having a quaternary carbon gave cyclized endo-olefins. This method was successfully applied to the synthesis of A-ring fragment of 1α, 25-dihydroxyvitamin D₃.

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