Synthetic investigations on illudinine: a new synthesis of methyl 8-methoxy-2,2-dimethyl-7-oxo-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate

Girija, Talupuru and Shanker, Sathya P and Rao, Subba GSR (1991) Synthetic investigations on illudinine: a new synthesis of methyl 8-methoxy-2,2-dimethyl-7-oxo-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate. In: Perkin Transactions 1 (6). pp. 1467-1471.

PDF Synthetic_Investigations_on_Illudinine.pdf - Published Version Restricted to Registered users only Download (757kB) | Request a copy

Abstract

A new strategy for the total synthesis of methyl 8-methoxy-2,2-dimethyl-7-oxo-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate 4, a key intermediate in the synthesis of illudalanes, is reported. The key step in this strategy is a new method of preparation of indanones from tetralones. Thus, the furfurylidene derivative of 6-methoxy-3,4-dihydronaphthalen-1-(2H)-one is oxidised to the dicarboxylic acid 9a which is cyclodehydrated to methyl 7-methoxy-1-oxoindan-4-carboxylate 10. Similar reactions on the tetrahydronaphthalenone 25, obtained from 6-methoxy-1,2,3,4-tetrahydronaphthalene-7-carbaldehyde 11 by sequential transformations including a regiospecific benzylic oxidation resulted in the hexahydro-s-indacenone 4, thus completing a formal synthesis of illudinine 1.

Item Type:	Journal Article
Publication:	Perkin Transactions 1
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	07 Dec 2010 09:03
Last Modified:	07 Dec 2010 09:03
URI:	http://eprints.iisc.ac.in/id/eprint/34215

Actions (login required)

View Item