title: Total Synthesis of Reported Structure of Baulamycin A and Its Congeners.
abstract: A convergent and flexible strategy for the stereoselective total synthesis of the reported structure of baulamycin A and its congeners has been developed for the first time. Synthetic highlights include a Crimmins aldol reaction to construct the C-1' and C-14 centers, a Crimmins acetate aldol reaction to generate the hydroxy group at the C-13 position, Horner-Wadsworth-Emmons olefination to form the C9-C10bond, and Evans methylation to install the C-8 center. This synthetic study disclosed that the reported structure of baulamycin A needs to be revised, as its spectroscopic data are not identical with those of the synthetic baulamycin A.
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Sandip
authors.initials: S
authors.lastname: Guchhait
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Shamba
authors.initials: S
authors.lastname: Chatterjee
authors.affiliation: NMR Unit, SAIF, CSIR-Central Drug Research Institute , Lucknow 226031, India.
authors.forename: Ravi Sankar
authors.initials: RS
authors.lastname: Ampapathi
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Rajib Kumar
authors.identifier: 0000-0001-7486-0618
authors.initials: RK
authors.lastname: Goswami
mesh_terms: D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012118:Resorcinols / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; D012118:Resorcinols; C000625678:baulamycin A