An efficient construction of bridged chiral tetracyclic indolidines, a core structure of asperparaline, via stereocontrolled catalytic Pauson–Khand reaction

A reaction of chiral enyne 22 derived from l-proline with a catalytic amount of cobalt (0) octacarbonyl in the presence of N-methylmorphorine N-oxide gave tricyclic enone 24 in 54% yield (73% based on consumed starting material). Treatment of enone 11 with aqueous methylamine followed by silica gel...

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Bibliographic Details
Published in:Tetrahedron 2005-02, Vol.61 (9), p.2481-2492
Main Authors: Tanimori, Shinji, Sunami, Tatsuya, Fukubayashi, Kouji, Kirihata, Mitsunori
Format: Article
Language:English
Subjects:
Asperparaline
Indolidine alkaloid
Paralytic activity
Pauson–Khand reaction
Spiro-succinimide
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Summary:A reaction of chiral enyne 22 derived from l-proline with a catalytic amount of cobalt (0) octacarbonyl in the presence of N-methylmorphorine N-oxide gave tricyclic enone 24 in 54% yield (73% based on consumed starting material). Treatment of enone 11 with aqueous methylamine followed by silica gel afforded bridged tetracyclic indolidine 1 , a common structural motif of natural metabolites, an asperparaline series of compounds and also a potential intermediate for the synthesis of a paralytic alkaloid, asperparaline C ( 4 ), in 70% yield. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.12.057