Work

A Minimalist NMR Approach for the Structural Revision of Mucoxin

Year: 2010

Type: article

Abstract: In an attempt to revise the structural assignment of mucoxin, and faced with 64 diastereomeric possibilities, we resorted to the synthesis of truncated structures that contained the core stereochemical sites. Twelve stereochemical analogues were synthesized, their (1)H and (13)C NMR spectra were analyzed and four recurring stereochemical trends were distilled from the data. Applying the observed trends to the diastereomeric population pared the possible choices for the correct structure of mucoxin from 64 to 4. Synthesis of these analogues led to the identification of the correct structure of mucoxin.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.201001619

Authors: Jun Yan, Atefeh Garzan, Radha S. Narayan, Chrysoula Vasileiou, Babak Borhan

Institution: Michigan State University

Language: English

Topic: Molecular spectroscopy and chirality

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Regio and Stereoselective Reactions in Synthesis of Heterocycles