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Communication | Regular issue | Vol 27, No. 5, 1988, pp.1135-1139
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4477
A New Synthesis of (—)-Isopretronecanol and (—)-Trachelanthamidine through Orthoester Claisen Rearrangement for Allylic Alcohol Functionality Tagged at C(2) of Pyrrolidine as a Key Step

Toshio Moriwake,* Shin-ichi Hamano, and Seiki Saito*

*Department of Applied Chemistry, Faculty of Engineering, Okayama Universityg, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

Orthoester Claisen rearrangement of (2S)-2-[1’(E)-3’-hydroxypropenyl]-Pyrrolidine derived from (S)-proline gave (2S)-2-[1’-(ethoxycarbonylmethyl)-2’- propenyl]-N-(t-butoxycabonyl)-pyrrolidin which is ready for further elaboration directed to necine base skeleton. Title compounds have been synthesized using this key intermediate.