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Communication | Special issue | Vol 17, No. 1, 1982, pp.53-57
Published online, 1st January, 1970
DOI: 10.3987/S-1982-01-0053
Modification of α-Santonin VII. Synthesis of Z-4-Germacranolide

Takeshi Shimizu, Masahiro Saito, Yukinori Ohgoshi, Yasuo Fujimoto* and Takashi Tatsuno

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan

Abstract

Z-4-germacranolides (heliangolides) were synthesized from α-santonin. The regio- and stereoselective introduction of Z-4-double bond info the cyclodecane ring required for the synthesis of naturally occurring heliangolide is performed in excellent yield via 5S-iodo derivatives of Z-9-germacranolides.