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Synlett 2001; 2001(7): 1113-1116
DOI: 10.1055/s-2001-15151
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Asymmetric Synthesis of (R)-Limonene and (S)-Cembrene-A by an Intramolecular Cyclization Reaction Using a Chiral Leaving Group

Kazuaki Ishihara* , Hiroko Nakamura, Hisashi Yamamoto
  • *Graduate School of Engineering, Nagoya University, CREST, Japan Science of Technology (JST), Furo-cho, Chikusa, Nagoya 464-8603, Japan; Fax + 81-52-789-32 22; E-mail: yamamoto@cc.nagoya-u.ac.jp
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Publication Date:
31 December 2001 (online)

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A six-membered monocyclic terpene, (R)-limonene, and a 14-membered monocyclic diterpene, (S)-cembrene-A, have been synthesized, respectively, by new enantioselective intramolecular cyclization reactions of neryl ether and (all-E)-geranylgeranyl ether using an (R)-1,1'-binaphthyl-2-benzoxy-2'-oxy auxiliary as a chiral leaving group in the presence of tin(IV) chloride.

limonene - cembrene-A - chiral leaving group - intramolecular cyclization - asymmetric synthesis