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Synthesis of (+)- and (-)-monanchorin
Journal article   Open access   Peer reviewed

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

Min Yu and Barry B Snider
Organic letters, Vol.11(4), pp.1031-1032
02/19/2009
DOI: https://doi.org/10.1021/ol802981h
PMCID: PMC2661423
PMID: 19166346

Abstract

Guanidines - chemistry Animals Stereoisomerism Antineoplastic Agents - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Guanidines - chemical synthesis Nuclear Magnetic Resonance, Biomolecular Molecular Structure Catalysis Antineoplastic Agents - chemistry Porifera - chemistry Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
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.
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https://doi.org/10.1021/ol802981hView
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