Polyphosphate ester-catalysed cyclodehydration of monoesters of N-substituted 3-(indol-3′-yl)-5-methylcyclohex-4-ene-1,2-dicarboxylic acids; stereoselective synthesis of methyl 9-methyl-6-oxo-5-tosyl-5,6,6aβ, 7β,8,10aβ-hexahydroindeno[2,1-b]indole-7α-carboxylate

Kin Fai Cheng, Tze Tat Wong, Wing Tak Wong, Ting Fong Lai

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The effect of the N-substituents on the polyphosphate ester-(PPE)-catalysed cyclodehydration of a monoester of N-substituted 5-methyl-3-(indol-3′-yl) cyclohex-4-ene-1,2-dicarboxylic acids (41) is presented. Stereoselective synthesis of methyl 9-methyl-6-oxo-5-tosyl-5,6,6aβ,7β,8,10aβ-hexahydroindeno[ 2,1-b]indole-7α-carboxylate (2), the key synthetic intermediate for C(7)-functionalized antifertility agent yuehchukene (YCK) (1) analogues, is described.
Original languageEnglish
Pages (from-to)2487-2496
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number9
Publication statusPublished - 1 Dec 1990
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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