Unknown

Dataset Information

0

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.

SUBMITTER: Zhong HM 

PROVIDER: S-EPMC2517629 | biostudies-literature | 2007 Jan

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Studies toward the asymmetric synthesis of the right part of the mycalamides.

Zhong H Marlon HM   Sohn Jeong-Hun JH   Rawal Viresh H VH  

The Journal of organic chemistry 20070101 2

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 i  ...[more]

Similar Datasets

Unknown Progress toward a Convergent, Asymmetric Synthesis of Jervine.
| S-EPMC7212305 | biostudies-literature
Unknown Progress toward the De Novo Asymmetric Synthesis of Euphanes.
| S-EPMC9419992 | biostudies-literature
Unknown Studies toward the synthesis of maoecrystal V.
| S-EPMC3373731 | biostudies-literature
Unknown Studies toward the total synthesis of pluraflavin A.
| S-EPMC4795151 | biostudies-literature
Unknown Studies directed toward the synthesis of the massileunicellins. 2.
| S-EPMC3111956 | biostudies-literature
Unknown Studies Directed toward the Stereoselective Synthesis of Cytospolide E.
| S-EPMC6641448 | biostudies-literature
Unknown Synthetic studies toward the mannopeptimycins: synthesis of orthogonally protected beta-hydroxyenduracididines.
| S-EPMC2871400 | biostudies-literature
Unknown Diastereoselective synthesis of cyclopentapyridazinones via radical cyclization: synthetic studies toward halichlorine.
| S-EPMC2745910 | biostudies-literature
Unknown Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.
| S-EPMC2756537 | biostudies-literature
Unknown Studies toward the synthesis of phomactin A. An approach to the macrocyclic core.
| S-EPMC2031845 | biostudies-literature