title: Total Synthesis of Oridamycins A and B.
abstract: The total synthesis of both oridamycin A and oridamycin B was accomplished starting from a common synthetic intermediate readily prepared from geranyl acetate. The sequence utilizes an oxidative radical cyclization to construct the trans-decalin ring system, setting three of four contiguous stereocenters in one operation. The carbazole nucleus was forged through a one-pot process entailing acid-promoted dehydration followed by 6π-electrocyclization/aromatization.
authors.affiliation: Tri-Institutional PhD Program in Chemical Biology, Laboratory for Bioorganic Chemistry, Memorial Sloan Kettering Cancer Center, Sloan Kettering Institute, 1275 York Avenue, New York, New York 10065, United States.
authors.forename: Adam H
authors.initials: AH
authors.lastname: Trotta
mesh_terms: D000085:Acetates / Q000737:chemistry; D000080462:Acyclic Monoterpenes; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry
chemical_list: D000085:Acetates; D000080462:Acyclic Monoterpenes; D012717:Sesquiterpenes; D013729:Terpenes; C549674:oridamycin A; C549675:oridamycin B; C432872:geranyl acetate