Synthesis of (+)- and (-)-monanchorin.
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.
Yu
Min
M
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Snider
Barry B
BB
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006146:Guanidines; C488575:monanchorin