Details

Autor(en) / Beteiligte

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

Titel

A Minimalist NMR Approach for the Structural Revision of Mucoxin

Ist Teil von

• Chemistry : a European journal, 2010-12, Vol.16 (46), p.13749-13756

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2010

Quelle

Wiley InterScience Journals

Beschreibungen/Notizen

• 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 1H and 13C 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. Annonaceous acetogenins: Analysis of the NMR spectra of 12 stereoisomeric analogues of mucoxin led to a number of structural constraints, limiting the field of diastereomeric possibilities from 64 to 4. This led to the identification of the relative stereochemistry of mucoxin.