A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine

Masahiro Bohno; Hidetomo Imase; Noritaka Chida

doi:10.1039/B402762K

A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine

Masahiro Bohno,^a Hidetomo Imase^a and Noritaka Chida*^a

* Corresponding authors

^a Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Japan
E-mail: chida@applc.keio.ac.jp
Fax: 81 45 566 1573
Tel: 81 45 566 1573

Abstract

The stereoselective and chiral synthesis of the Amaryllidaceae alkaloid, (+)-vittatine 1, is described; the quaternary carbon in 1 was generated by Claisen rearrangement of a cyclohexenol derived from D-glucose by way of a Ferrier's carbocyclisation reaction and a hexahydroindole skeleton was effectively constructed by intramolecular aminomercuration–demercuration, followed by Chugaev reaction.

Supplementary files

Publication details

The article was received on 23 Feb 2004, accepted on 11 Mar 2004 and first published on 30 Mar 2004

Article type: Communication

DOI: 10.1039/B402762K

Citation: Chem. Commun., 2004,0, 1086-1087

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A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine

M. Bohno, H. Imase and N. Chida, Chem. Commun., 2004, 0, 1086
DOI: 10.1039/B402762K
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Chemical Communications

A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine

Abstract

Supplementary files

Publication details

A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine

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