Sequential Suzuki/Suzuki Couplings with a Dibromoiododiene - A Versatile Strategy for the Stereocontrolled Synthesis of Polyunsaturated Butenolides

Inken Hanisch; Reinhard Brückner

doi:10.1055/s-2000-6528

Synlett 2000; 2000(3): 374-378
DOI: 10.1055/s-2000-6528

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Sequential Suzuki/Suzuki Couplings with a Dibromoiododiene - A Versatile Strategy for the Stereocontrolled Synthesis of Polyunsaturated Butenolides

Inken Hanisch^* , Reinhard Brückner

^*Institut für Organische Chemie, Georg-August-Universität, Tammannstr. 2, D-37077 Göttingen, Germany; Fax +49-7 61-2 03 61 00; E-mail: reinhard.brueckner@organik.chemie.uni-freiburg.de

Abstract

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In the presence of NaOH and cat. Pd(PPh₃)₄, the trihalodiene 4 underwent highly regioselective Suzuki-couplings with unsaturated boronic acids: At 70 °C, the iodoolefin moiety coupled first (with boronic acid 14) and the E-bromoolefin moiety thereafter (with boronic acid 16). The resulting Z-bromolefin 17 was transformed into the stereopure α-alkenyl-γ-alkylidenebutenolide 2 in three steps. The strategy developed here should be applicable to the synthesis of peridinin (1) which plays a central role in photosynthesis by marine algae.

butenolides - C-C couplings - furanones - stereoselective synthesis - Suzuki couplings

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