Issue 5, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry

Hisahiro Hagiwara,*a   Hitoshi Sakai,a   Takashi Uchiyama,a   Yoshiaki Ito,b   Noriyuki Morita,b   Takashi Hoshi,b   Toshio Suzukib  and  Masayoshi Andob  

* Corresponding authors

a Graduate School of Science and Technology, Niigata University, 8050, 2-nocho, Ikarashi, Niigata 950-2181, Japan

b Faculty of Engineering, Niigata University, 8050, 2-nocho, Ikarashi, Niigata 950-2181, Japan

Abstract

The tetracyclic sesquiterpenoid (+)-cyclomyltaylan-5α-ol 1 has been synthesized starting from (S)-(+)-Hajos–Wiechert ketone analogue 10via stereoselective Claisen rearrangement followed by SmI2-promoted reductive cyclisation. Thus, the absolute configuration has been established to be 2R,3R,4R,5S,6R,7R (cyclomyltaylane numbering) as depicted in structure 1.

Graphical abstract: The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry

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Article information

DOI
https://doi.org/10.1039/B111594B
Article type
Paper
Submitted
19 Dec 2001
Accepted
16 Jan 2002
First published
05 Feb 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 583-591

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The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry

H. Hagiwara, H. Sakai, T. Uchiyama, Y. Ito, N. Morita, T. Hoshi, T. Suzuki and M. Ando, J. Chem. Soc., Perkin Trans. 1, 2002, 583 DOI: 10.1039/B111594B

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