… of inverto-yuehchukene and its 10-(indol-3′-yl) isomer. X-Ray structure of (4a RS, 10a RS)-1, 1, 3-trimethyl-1, 2, 4a, 5, 10, 10a-hexahydroindene [1, 2-b] indol-10- …

KF Cheng, MK Cheung

Index: Cheng, Kin-Fai; Cheung, Man-Ki Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 11 p. 1213 - 1218

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Citation Number: 15

Abstract

A total synthesis of inverto-yuehchukene 4 and its 10-(indo-3′-yl) isomer 7 is described. The key tetracyclic ketone intermediate 13 was synthesized by a coupling reaction between 3-indolylzinc reagent and acid chloride 11, followed by Nazarov cyclization of the divinyl ketone 12. The indol-2-yl moiety present in inverto-yuehchukene 4 was introduced by palladium (0)-catalysed cross-coupling between indol-2-ylzinc reagent and the acetate 16.