Issue 0, 1979

Polycyclic systems. Part 19. Synthesis of 8-isobutyl-10-methyl-11H-indeno[2,1-a]phenanthrene (second diels hydrocarbon), a minor dehydrogenation product of cholesterol

Abstract

The structure of the second Diels hydrocarbon, a dehydrogenation product of cholesterol, has been confirmed as 8-isobutyl-10-methyl-11H-indeno[2,1-a]phenanthren(1) by an unambiguous synthesis. 4-Isobutyl-2-methyl-1-bromobenzene (5) prepared from m-acetotoluidide was converted by a series of standard reactions into 2,4-dimethyl-6-isobutylindan-1-one (10) which on condensation with 2-(1-naphthyl)ethylmagnesium bromide followed by cyclisation and dehydrogenation afforded the desired hydrocarbon (1), identical with the second Diels hydrocarbon in all respects.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 3034-3036

Polycyclic systems. Part 19. Synthesis of 8-isobutyl-10-methyl-11H-indeno[2,1-a]phenanthrene (second diels hydrocarbon), a minor dehydrogenation product of cholesterol

D. Nasipuri, A. K. Samaddar and I. Datta, J. Chem. Soc., Perkin Trans. 1, 1979, 3034 DOI: 10.1039/P19790003034

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