title: Studies toward the asymmetric synthesis of the right part of the mycalamides.
abstract: Described herein is the asymmetric synthesis of a functionalized, trioxadecalin unit that comprises the right-hand part of the mycalamides and related natural products. The synthetic route involves a 16-step sequence that accomplishes the formation of two heterocyclic rings and the generation of five stereocenters. The synthesis commenced with a C2-symmetric starting material, diethyl D-tartrate, and took advantage of a relay of diastereoselective reactions to extend this four-carbon chain and introduce new chiral centers. Subsequent electrophile-mediated cyclization afforded the desired pyran ring, which was then transformed into the desired, functionalized trioxadecalin skeleton.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: H Marlon
authors.initials: HM
authors.lastname: Zhong
authors.forename: Jeong-Hun
authors.initials: JH
authors.lastname: Sohn
authors.forename: Viresh H
authors.initials: VH
authors.lastname: Rawal
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D011714:Pyrans; C059647:mycalamide B; C059646:mycalamide A