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Stereocontrolled Synthesis of (11Z)-Retinal and Its Analogues

1998; Wiley; Volume: 37; Issue: 3 Linguagem: Inglês

10.1002/(sici)1521-3773(19980216)37

1521-3773

Jun’ichi Uenishi, Reiko Kawahama, Osamu Yonemitsu, Akimori Wada, Masayoshi Ito,

Retinal and Macular Surgery

Suzuki coupling of stereochemically pure (Z)-bromotetraene 1—which is extremely unstable but can be kept in frozen benzene in the presence of a small amount of PPh3 at &sminus 01;20°C—and (Z)-alkenylboronic acid 2 provides the stereocontrolled synthesis of (11Z)-retinal 3. The 11Z configuration, which is introduced by selective catalytic debromination of the corresponding dibromo precursor of 1, is retained in this step. TBDMS = tBuMe2Si.