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

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

Research output: Journal article publication › Journal article › Academic research › peer-review

Abstract

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 language	English
Pages (from-to)	2487-2496
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	9
Publication status	Published - 1 Dec 1990
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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Cheng, K. F., Wong, T. T., Wong, W. T., & Lai, T. F. (1990). 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. Journal of the Chemical Society, Perkin Transactions 1, (9), 2487-2496.

Cheng, Kin Fai ; Wong, Tze Tat ; Wong, Wing Tak et al. / 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. In: Journal of the Chemical Society, Perkin Transactions 1. 1990 ; No. 9. pp. 2487-2496.

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title = "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",

abstract = "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.",

author = "Cheng, {Kin Fai} and Wong, {Tze Tat} and Wong, {Wing Tak} and Lai, {Ting Fong}",

year = "1990",

month = dec,

day = "1",

language = "English",

pages = "2487--2496",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

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Cheng, KF, Wong, TT, Wong, WT & Lai, TF 1990, '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', Journal of the Chemical Society, Perkin Transactions 1, no. 9, pp. 2487-2496.

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. / Cheng, Kin Fai; Wong, Tze Tat; Wong, Wing Tak et al.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 9, 01.12.1990, p. 2487-2496.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - 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

AU - Cheng, Kin Fai

AU - Wong, Tze Tat

AU - Wong, Wing Tak

AU - Lai, Ting Fong

PY - 1990/12/1

Y1 - 1990/12/1

N2 - 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.

AB - 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.

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M3 - Journal article

SN - 1472-7781

SP - 2487

EP - 2496

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 9

ER -

Cheng KF, Wong TT, Wong WT, Lai TF. 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. Journal of the Chemical Society, Perkin Transactions 1. 1990 Dec 1;(9):2487-2496.

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

Abstract

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