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Communication | Regular issue | Vol 65, No. 3, 2005, pp.531-540
Published online, 21st January, 2005
DOI: 10.3987/COM-04-10317
Studies toward the Synthesis of Furanocembrane Bipinnatin J: Synthesis of a 2,3,5-Trisubstituted Furfuryl Ether Intermediate

Masayoshi Tsubuki,* Kazunori Takahashi, Ken Sakata, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Synthesis of 2,3,5-trisubstituted furfuryl ether (29), a potential intermediate in a synthetic approach to bipinnatin J, was achieved by a combination of etherification and Stille cross-coupling reaction. Unexpectedly, an intramolecular coupling reaction of 29 proceeded through SN2’ substitution to give 15-membered furfuryl ether (30). Formation of γ-butenolide (34) was also accomplished by a ruthenium-catalyzed carbonylation of allenic alcohol (33).