Total synthesis of a macrocyclic pyrrolizidine alkaloid,(.+-.)-integerrimine, utilizing an activable protecting group

…, T Uchimaru, D Guedin-Vuong

Index: Narasaka, Koichi; Sakakura, Toshiyasu; Uchimaru, Tadafumi; Guedin-Vuong, Denis Journal of the American Chemical Society, 1984 , vol. 106, # 10 p. 2954 - 2961

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Citation Number: 78

Abstract

Abstract: A new esterification reaction has been developed utilizing a (methy1thio) methyl (MTM) group as an activable protecting group of carboxylic acid. A total synthesis of a 12- membered pyrrolizidine alkaloid,(&)-integerrimhe (l), has been achieved by applying the above method to formation of the macrocyclic bislactone skeleton. The acid anhydride (la) of the integerrinecic acid derivative was coupled with lithium alkoxide of retronecine silyl ...