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Org Lett. 2009 Feb 19;11(4):1031-2. doi: 10.1021/ol802981h.

Synthesis of (+)- and (-)-monanchorin.

Author information

1
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.

Abstract

The optically pure epoxy acetal was converted to the protected guanidino alcohol by reaction with NaN(3) in DMF, hydrogenation of the azide, and reaction of the amine with MeSC(NBoc)NHBoc, AgNO(3), and Et(3)N. Treatment of the protected guanidino alcohol with 9:1 CDCl(3)/TFA afforded monanchorin, whose absolute stereochemistry was assigned as shown.

PMID:
19166346
PMCID:
PMC2661423
DOI:
10.1021/ol802981h
[Indexed for MEDLINE]
Free PMC Article

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