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DOI: 10.1039/A703212I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 3665-3672

Neurosteroid analogues. Part 5.1 Enantiomers of neuroactive steroids and benz[e]indenes: total synthesis, electrophysiological effects on GABAA receptor function and anesthetic actions in tadpoles

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Yuefei Hu, Lisa L. Wittmer, Melissa Kalkbrenner, Alex S. Evers, Charles F. Zorumski and Douglas F. Covey

Abstract

The synthesis of (3β,5β,8α,9β,10α,13α,14β,17α)-3-hydroxypregnan-20-one 2, (3β,5β,8α,9β,10α,13α,14β,17α)-3-hydroxyandrostane-17-carbonitrile 4,† [3R-(3α,3aα,5aβ,7α,9aα,9bβ)]-1-[dodecahydro-7-(2-hydroxyethyl)-3a-methyl-1H-benz[e]inden-3-yl]ethanone 6 and [3R-(3α,3aα,5aβ,7α,9aα,9bβ)]-dodecahydro-7-(2-hydroxyethyl)-3a-methyl-1H-benz[e]indene-3-carbonitrile 8 is reported.‡ Steroids 2 and 4 have been used previously to investigate the enantioselectivity of steroid action on GABAA receptor function and to correlate steroid action at this receptor with the anesthetic actions of the compounds. The enantioselective actions of benz[e]indenes 6 and 8 have been evaluated for the same reasons in this study. Similar correlations between the enantioselective effects of both classes of compounds on GABAA receptor function and anesthetic potency in tadpoles have been observed.

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