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Synlett 1998; 1998(6): 679-681
DOI: 10.1055/s-1998-1751
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Diastereoselective Synthesis of (2S*,3R*)- and (2R*,3R*)-2,6-Dimethyl-2-homoprenylchroman-3-ol

Seiichi Inoue* , Masatoshi Asami, Kiyoshi Honda, Kedar Shanker Shrestha, Masaaki Takahashi, Takashi Yoshino
  • *Department of Synthetic Chemistry, Faculty of Engineering, Yokohama National University, Tokiwadai, Hodogayaku, Yokohama 240-8501, Japan; Fax 045-339-3970; E-mail: inoue@syn.synchem.bsk.ynu.ac.jp
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Publication Date:
31 December 2000 (online)

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Diastereoselective synthesis of (2S*,3R*)- and (2R*,3R*)-2,2-dialkylchroman-3-ols was achieved by stereoselective epoxide-opening cyclization of ortho-(2,3-epoxyalkyl)phenols which were prepared by the coupling of p-cresol and (2R*,3R*)- and (2R*,3S*)-2,3-diacetoxyalkyl isopropyl sulfides, which were in turn derived from geraniol and nerol, respectively.

chroman - ortho-alkylation - diastereoselective synthesis - [2,3]sigmatropic rearrangement