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Communication | Special issue | Vol 82, No. 2, 2010, pp.1163-1170
Published online, 18th November, 2010
DOI: 10.3987/COM-10-S(E)111
[2,3] Wittig Rearrangement of β’-Hydroxyethyl Bis-Allylic Ethers: Highly Regiospecific Entry to Singly Dehydroxylated 19-Nor-1(or 3),25-dihydroxy-vitamin D3

Koichi Mikami,* Kumiko Fujita, Kazuki Wakabayashi, and Shigekazu Ito

*Department of Applied Chemistry, Graduate School of Science and Technology, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan

Abstract

A conceptually new approach to regiospecific deprotonation at the α-position of β'-hydroxyethyl bis-allylic ethers is shown on the basis of the dianion repulsion with the β'-alkoxy anion, of which the [2,3]Wittig rearrangement product can be transformed to the A-rings of singly dehydroxylated 1(or 3),25-dihydroxy-19-nor-vitamin D3 analogues to stimulate apoptosis or differentiation of HL-60 cancer cell.