Total synthesis of (-)-ulapualide A: The danger of overdependence on NMR spectroscopy in assignment of stereochemistry

被引：41

作者：

Pattenden, Gerald ^{[1
]}

Ashweek, Neil J. ^{[1
]}

Baker-Glenn, Charles A. G. ^{[1
]}

Walker, Gary M. ^{[1
]}

Yee, James G. K. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 23期

关键词：

macrocycles; natural products; oxazoles; structure elucidation; total synthesis;

D O I：

10.1002/anie.200700459

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lessons learnt: The asymmetric total synthesis of the macrolide (-)-ulapualide A has been accomplished. Interestingly, the 1H NMR spectrum and chiroptical data of the macrolide and of a previously synthesized diastereoisomer with opposite stereocenters at C3, C28, C29, C30, and C32 were superimposable, which highlights the care that must be taken in the assignment of configurations to complex structures based on NMR spectroscopy. (Chemical Equation Presented) © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4359 / 4363

页数：5

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