Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system. Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212).
The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483A (5). Aldol reaction of hydroxybutanolides 13b,c with 2,4-hexadienal affords 12b,c, which are subjected to iodoetherification with bis(sym-collidine)IPF6 to provide 11b(c). Treatment with Et3N in CH2Cl2 completes the three-step syntheses of TAN-2483A (5) and waol A (6). Aldol reaction of hydroxybutanolide 31 with 2,4-hexadienal affords 32, which is subjected to iodoetherification to provide 34, which in turn is treated with Bu3SnCl, NaBH3CN, and oxygen to provide diol 60. Further elaboration completes the first syntheses of massarilactone B (7) and the fusidilactone B (9) ring system.
Gao
Xiaolei
X
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Snider
Barry B
BB
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / 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; C490945:fusidilactone B; C490946:massarilactone B; C420729:waol B