A tandem radical macrocyclisation-transannular cyclisation approach towards the taxanes

SA Hitchcock, SJ Houldsworth, DC Pryde…

Index: Hitchcock, Stephen A.; Houldsworth, Stephen J.; Pattenden, Gerald; Pryde, David C.; Thomson, Nicholas M.; Blake, Alexander J. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 19 p. 3181 - 3206

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Citation Number: 34

Abstract

Separate treatment of the iodotrienedione 19 and the iododienynedione 38 with Bu 3 SnH– AIBN produces the corresponding taxane ring systems 25 (25–30%) and 56 (50–60%) respectively by way of tandem radical macrocyclisation-radical transannular cyclisations. By contrast the analogous iodopolyenones 61, 63, 65a, 66a, 86a and 87a, together with the corresponding iodoenynones 39a and 59 failed to undergo similar tandem radical ...