Synthesis of (-)-TAN-2483A. Revision of the structures and syntheses of (+/-)-FD-211 (waol A) and (+/-)-FD-212 (waol B).
[structure: see text] 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)IPF(6) to provide 8b(c). Treatment with Et(3)N in CH(2)Cl(2) completes three-step syntheses of TAN-2483A (5) and waol A (6).
Gao
Xiaolei
X
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Nakadai
Masakazu
M
Snider
Barry B
BB
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000970:Antineoplastic Agents; C092867:FD 211; D005663:Furans; D007783:Lactones; C475530:TAN-2483A; C420729:waol B