Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang
University, Hangzhou 310027, China, and Department of Chemistry, The Hong Kong
University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR,
China
chdai@ust.hk; chdai@zju.edu.cn
Received May 10, 2007
Abstract:
Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis
to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chiral synthons with the
tetrahydrofuran ring formed via 5-endo epoxide ring-opening cyclization. It was found that the C6-keto seco substrate showed higher reactivity
toward Grubbs' second generation catalyst while Schrock's Mo catalyst was completely inactive for formation of the macrocycle.
