Synthesis of (−)-TAN-2483A. Revision of
the Structures and Syntheses of
(±)-FD-211 (Waol A) and (±)-FD-212
(Waol B)

Gao, Xiaolei; Nakadai, Masakazu; Snider, Barry B.

doi:10.1021/ol0273405.s001

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Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)

journal contribution

posted on 2003-01-30, 00:00 authored by Xiaolei Gao, Masakazu Nakadai, Barry B. Snider

The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483 A (5). Aldol reaction of 10b(c) with 2,4-hexadienal (11) affords 9b(c), which is subjected to iodoetherification with bis(sym-collidine)IPF₆ to provide 8b(c). Treatment with Et₃N in CH₂Cl₂ completes three-step syntheses of TAN-2483A (5) and waol A (6).