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Synthesis of the 1-phenethyltetrahydroisoquinoline alkaloids (+)-dysoxyline, (+)-colchiethanamine, and (+)-colchiethine.

Authors
  • Reddy, Raju Jannapu1
  • Kawai, Nobuyuki
  • Uenishi, Jun'ichi
  • 1 Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan. , (Japan)
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Dec 21, 2012
Volume
77
Issue
24
Pages
11101–11108
Identifiers
DOI: 10.1021/jo302157e
PMID: 23176065
Source
Medline
License
Unknown

Abstract

Asymmetric total syntheses of the 1-phenethyl-1,2,3,4-tetrahydroisoquinoline alkaloids (+)-dysoxyline (1), (+)-colchiethanamine (2), and (+)-colchiethine (3) are described. In the synthetic routes, coupling of a key, enatiomerically pure 1-(sulfonylmethyl)tetrahydroisoquinoline with aromatic aldehydes, performed by using the Julia-Kocienski reaction, afforded the corresponding 1-(β-styryl)-substituted tetrahydroisoquinolines with complete retention of the absolute configuration at the C1 carbon atom. Functionalization of the products generated in these processes by using four- or five-step sequences gave the target alkaloids 1-3.

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