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Communication | Special issue | Vol 77, No. 2, 2009, pp.829-835
Published online, 22nd September, 2008
DOI: 10.3987/COM-08-S(F)100
Synthesis of 2-Methylene-tetrahydropyran-3-ol Derivative, a Key Segment for Convergent Synthesis of Polycyclic Ethers Based on Suzuki-Miyaura Coupling

Tomohiro Kimura, Yasuyo Miyagawa, Shingo Ozawa, Mayumi Hagiwara, and Tadashi Nakata*

*Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

2-Methylene-tetrahydropyran-3-ol derivative, a key segment for convergent synthesis of polycyclic ethers based on Suzuki-Miyaura coupling, was efficiently synthesized by two methods; (1) via SmI2-induced reductive cyclization of β-alkoxyvinyl sulfone with aldehyde followed by elimination of the sulfonyl group, and (2) via SmI2-induced cyclization of β-alkoxyvinyl sulfoxide with aldehyde followed by dehydration of the 2-hydroxymethyl group.