First total synthesis of a novel monoterpenoid isoquinoline alkaloid, (+/-)-alangine

Hiromitsu Takayama; Maki Arai; Mariko Kitajima; Norio Aimi

doi:10.1248/cpb.50.1141

First total synthesis of a novel monoterpenoid isoquinoline alkaloid, (+/-)-alangine

Chem Pharm Bull (Tokyo). 2002 Aug;50(8):1141-3. doi: 10.1248/cpb.50.1141.

Authors

Hiromitsu Takayama¹, Maki Arai, Mariko Kitajima, Norio Aimi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan. h.takayama@p.chiba-u.ac.jp

PMID: 12192157
DOI: 10.1248/cpb.50.1141

Abstract

The structure including the stereochemistry of a novel monoterpenoid isoquinoline alkaloid, alangine, was confirmed by total synthesis via N-acyliminium cyclization to construct the isoquinoline skeleton and reductive cleavage of vinyl epoxide with Pd(0) catalyst.

Publication types

Letter

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Monoterpenes / chemical synthesis*
Monoterpenes / chemistry
Stereoisomerism

Substances

Alkaloids
Isoquinolines
Monoterpenes
alangine