Total Synthesis of (-)- and (+)-dysibetaine

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2001 Jun 19

PMID 11405705

Citations 4

Authors

B B Snider

Y Gu

Affiliations

Soon will be listed here.

Abstract

Glycidamides 6R and 6S were elaborated to (R,R)- and (S,S)-dysibetaines (1R and 1S) by intramolecular alkylation and functional group modification in 23% overall yield. The absolute stereochemistry of natural dysibetaine was established as S,S by comparison of the optical rotation of the natural product with that of the synthetic materials.

Citing Articles

Dicarboxylic Acid Monoesters in β- and δ-Lactam Synthesis.

Ananeva A, Bakulina O, Darin D, Kantin G, Krasavin M Molecules. 2022; 27(8).

PMID: 35458663 PMC: 9032910. DOI: 10.3390/molecules27082469.

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines.

Seibel Z, Bandar J, Lambert T Beilstein J Org Chem. 2021; 17:2077-2084.

PMID: 34476014 PMC: 8381810. DOI: 10.3762/bjoc.17.134.

Theoretical Calculation and Experimental Verification Demonstrated the Impossibility of Finding Haptens Identifying Triphenylmethane Dyes and Their Leuco Metabolites Simultaneously.

Kong D, Lv F, Hu B, Cao L Molecules. 2018; 23(3.

PMID: 29543738 PMC: 6017731. DOI: 10.3390/molecules23030663.

Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Wardrop D, Burge M J Org Chem. 2005; 70(25):10271-84.

PMID: 16323835 PMC: 3308172. DOI: 10.1021/jo051252r.