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Paper | Special issue | Vol 77, No. 1, 2009, pp.433-444
Published online, 31st July, 2008
DOI: 10.3987/COM-08-S(F)40
Wittig Rearrangement of 3-Furylmethyl Ethers: Facile Synthesis of 3-Methyl-2-furylmethanols and 3-Furylethanols

Masayoshi Tsubuki,* Hiroyuki Okita, Kazunori Kaneko, Atsushi Shigihara, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Wittig rearrangement of 3-furylmethyl ethers 1a-i was investigated. Deprotonation of 3-furylmethyl ethers 1a-i with bases, such as BuLi and LDA, occurred preferentially at the allylic, propargylic, benzylic positions and α-position adjacent to carbonyl group giving the corresponding anions, which underwent 2,3- and 1,2-rearrangements to afford 3-methyl-2-furylmethanols 2a-i and 3-furylethanols 3a-f,h,i. Synthesis of naginata ketone and dendrolasin was achieved employing the Wittig rearrangement as a key step.