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Paper | Special issue | Vol 30, No. 2, 1990, pp.1101-1119
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S106
A Total Synthesis of (+)-Geodiamolides A and B, the Novel Cyclodesiprptides

Yoshiro Hirai, Katsuyuki Yokota, Takao Yamzaki, and Takefumi Momose*

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

Diastereo-controlled total synthesis of (+)-geodiamolides A (1) and B (2) has been accomplished via a prior synthesis of the tetrapropionate-derived fragment 7 and of the halogenated N-methyltyrosyltripeptide 6, the latter involving direct halogenation of the tripeptide 5, and subsequent coupling of both fragments followed by the trichlorobenzoyl chloride-mediated macrolactonization, respectively.