Studies toward the asymmetric synthesis of the right part of the mycalamides.
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.
Zhong
H Marlon
HM
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Sohn
Jeong-Hun
JH
Rawal
Viresh H
VH
D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D011714:Pyrans; C059647:mycalamide B; C059646:mycalamide A