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J Am Chem Soc. 2013 Aug 28;135(34):12568-71. doi: 10.1021/ja406657v. Epub 2013 Aug 19.

Asymmetric total synthesis of neoxaline.

Author information

1
Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Tokyo 108-8641, Japan.

Abstract

A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.

PMID:
23957424
DOI:
10.1021/ja406657v
[Indexed for MEDLINE]

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