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Paper | Special issue | Vol 79, No. 1, 2009, pp.805-820
Published online, 20th November, 2008
DOI: 10.3987/COM-08-S(D)49
Total Synthesis of (–)-Flustramine B via One-Pot Intramolecular Ullmann Coupling and Claisen Rearrangement

Tomohiro Hirano, Kanako Iwakiri, Hiroshi Miyamoto, Atsuo Nakazaki, and Susumu Kobayashi*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

Total synthesis of (–)-flustramine B was achieved via one-pot intramolecular Ullmann coupling and Claisen rearrangement. A striking feature of this method of synthesis is that the sequential intramolecular Ullmann coupling and Claisen rearrangement reactions proceeds with concomitant deprotection of the methoxymethyl (MOM) group to afford spirocyclic oxindole with perfect asymmetric transmission in good overall yield.