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Letter

Asymmetric Synthesis of (−)-Adaline

Supporting Info

Toshimasa Itoh, Naoki Yamazaki, and Chihiro Kibayashi*

School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Org. Lett., 2002, 4 (15), pp 2469–2472

DOI: 10.1021/ol0200807

Publication Date (Web): June 29, 2002

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kibayasi@ps.toyaku.ac.jp

Abstract

An enantioselective total synthesis of (−)-adaline has been achieved starting from a chiral 6,6-disubstituted piperidone derivative previously prepared by diastereoselective allylation of a chiral tricyclic N-acyl-N,O-acetal. The key steps include lithium ion-activated S_N2-type alkynylation of the tricyclic N,O-acetal leading to exclusive formation of the (6S)-ethynylpiperidine and ring-closing olefin metathesis of the (2R,6S)-cis-2,6-dialkenylpiperidine for constructing the bridged azabicyclononane.

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Published In Issue July 25, 2002
Received April 18, 2002

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Letter

Asymmetric Synthesis of (−)-Adaline

Abstract

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