Stereoselective synthesis of the bicyclic guanidine alkaloid (+)-monanchorin.
A new approach for the stereoselective synthesis of the bicyclic guanidine alkaloid (+)-monanchorin has been developed using a palladium(ii)-catalysed MOM-ether directed Overman rearrangement to establish the second stereogenic centre and a cross metathesis reaction to generate the carbon backbone. In the final stage, a one-pot acid mediated deprotection of aldehyde, guanidine and hydroxyl groups gave an intermediate that underwent facile cyclisation to (+)-monanchorin.
Zaed
Ahmed M
AM
WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UKG12 8QQ.
Sutherland
Andrew
A
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006146:Guanidines; C488575:monanchorin