Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (−)-rosmarinecine

Shuji Akai; Kouichi Tanimoto; Yukiko Kanao; Sohei Omura; Yasuyuki Kita

doi:10.1039/B419426H

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Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (−)-rosmarinecine†

Shuji Akai,^a Kouichi Tanimoto,^a Yukiko Kanao,^a Sohei Omura^a and Yasuyuki Kita*^a

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Japan
E-mail: kita@phs.osaka-u.ac.jp
Fax: (+81) 6-6879-8229

Abstract

The title domino reactions were developed to directly provide tetrahydrofuro[3,4-c]isoxazole derivatives (5 and 9) in ≥90% ee from racemic α-hydroxynitrones (2 and 6), which were used in the concise asymmetric total synthesis of (−)-rosmarinecine 10.

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Supplementary files

Determination of the optical purity and absolute structure of ( S)-2, 5a,b, ( S)-6, 9 and 14 and typical procedures for the lipase-catalyzed domino reaction (Table 1, entry 5) and the one-pot synthesis of 5b (entry 7) PDF (185K)

Article information

DOI: https://doi.org/10.1039/B419426H
Article type: Communication
Submitted: 05 Jan 2005
Accepted: 28 Feb 2005
First published: 16 Mar 2005

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Chem. Commun., 2005, 2369-2371

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Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (−)-rosmarinecine

S. Akai, K. Tanimoto, Y. Kanao, S. Omura and Y. Kita, Chem. Commun., 2005, 2369 DOI: 10.1039/B419426H

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Chemical Communications

Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (−)-rosmarinecine†

Abstract

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Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (−)-rosmarinecine

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