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Radical-mediated synthesis of the 5,11-methanomorphanthridine ring system: formal total synthesis of montanine-type Amaryllidaceae alkaloids, (±)-montanine, (±)-coccinine and (±)-pancracine

Radical-mediated synthesis of the 5,11-methanomorphanthridine ring system: formal total synthesis of montanine-type Amaryllidaceae alkaloids, (±)-montanine, (±)-coccinine and (±)-pancracine

Authors :
Eiko Tanazawa
Miyuki Ishizaki
Ken-Ichi Kurihara
Osamu Hoshino
Source :
J. Chem. Soc., Perkin Trans. 1. :101-110
Publication Year :
1993
Publisher :
Royal Society of Chemistry (RSC), 1993.

Abstract

Radical-mediated reaction of the phenyl sulfide 16 and the phenyl selenide 17 in boiling toluene or o-xylene containing AIBN gave, in moderate yields, the 5, 11-methanomorphanthridine ring system 4, which is a basic skeleton of montanine-type Amaryllidaceae alkaloids, and formal total synthesis of the title alkaloids 1–3 by conversion of 5, 11-methanomorphanthridin-2-one 5, derived from N-(4-oxocyclohex-2-enyl)-4-phenylthiotetrahydroisoquinoline 21 using this methodology, into the 2,3-benzylidenedioxy-5,11-methanomorphanthridine 31 is achieved.

Details

ISSN :
13645463 and 0300922X
Database :
OpenAIRE
Journal :
J. Chem. Soc., Perkin Trans. 1
Accession number :
edsair.doi...........19f3a4682a30c57a6e578c4dfeb78695
Full Text :
https://doi.org/10.1039/p19930000101