Unknown

Dataset Information

0

A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.

ABSTRACT: The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product.

SUBMITTER: Bedke DK 

PROVIDER: S-EPMC2830791 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.

Bedke D Karl DK   Shibuya Grant M GM   Pereira Alban R AR   Gerwick William H WH   Vanderwal Christopher D CD  

Journal of the American Chemical Society 20100301 8

The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product. ...[more]

Similar Datasets

Unknown A concise enantioselective synthesis of (-)-ranirestat.
| S-EPMC2850125 | biostudies-literature
Unknown Concise, enantioselective total synthesis of (-)-alstonerine.
| S-EPMC2516964 | biostudies-literature
Unknown A concise enantioselective synthesis of the guaiane sesquiterpene (-)-oxyphyllol.
| S-EPMC3817518 | biostudies-literature
Unknown A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids.
| S-EPMC7185878 | biostudies-literature
Unknown Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles.
| S-EPMC6995259 | biostudies-literature
Unknown Concise and enantioselective total synthesis of (-)-mehranine, (-)-methylenebismehranine, and related Aspidosperma alkaloids.
| S-EPMC4240000 | biostudies-literature
Unknown Concise Enantioselective Total Synthesis of Cardiotonic Steroids 19-Hydroxysarmentogenin and Trewianin Aglycone.
| S-EPMC5015484 | biostudies-literature
Unknown Cross-Metathesis of Methallyl Halides: Concise Enantioselective Formal Total Synthesis of (-)-Presphaerene.
| S-EPMC7344242 | biostudies-literature
Unknown A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine?D and unnatural analogues.
| S-EPMC3540812 | biostudies-literature
Unknown Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.
| S-EPMC4651737 | biostudies-literature