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Stereoselective Synthesis of trans -Fused 7,6,6,7-Membered Tetracyclic Ether, Corresponding to the EFGH-Ring of Gambierol and the BCDE-Ring of Gambieric Acids

2008; American Chemical Society; Volume: 11; Issue: 1 Linguagem: Inglês

10.1021/ol8024555

1523-7060

Tatsuo Saito, Tadashi Nakata,

Marine Sponges and Natural Products

Stereoselective synthesis of a trans-fused 7,6,6,7-membered tetracyclic ether, corresponding to the EFGH-ring of gambierol and the BCDE-ring of gambieric acids, was efficiently accomplished via a two-directional approach. The key reactions were SmI2-induced double cyclization for construction of the F- and H-rings and SmI2-induced cyclization followed by ring expansion for construction of the E-ring.