title: 10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D.
abstract: The asymmetric synthesis of dragmacidin D (1) was completed in 10 steps. Its sole stereocenter was set by using direct asymmetric alkylation enabled by a C2-symmetric tetramine and lithium N-(trimethylsilyl)-tert-butylamide as the enolization reagent. A central Larock indole synthesis was employed in a convergent assembly of the heterocyclic subunits. The stereochemical evidence from this work strongly supports the predicted S configuration at the 6''' position, which is consistent with other members of the dragmacidin family of natural products.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106-9510 (USA).
authors.forename: Jeffrey J
authors.initials: JJ
authors.lastname: Jackson
authors.affiliation: Daiichi Sankyo Co., LTD, 1-2-58, Hiromachi, Shinagawa-ku, Tokyo 140-8710 (Japan).
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kobayashi
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106-9510 (USA).
authors.forename: Sophia D
authors.initials: SD
authors.lastname: Steffens
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106-9510 (USA). zakarian@chem.ucsb.edu.
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C470335:dragmacidin D
keywords: asymmetric synthesis; dragmacidin; heterocycles; indoles; total synthesis