Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products.
[structure: see text] Full details of the asymmetric total syntheses of the dibenzocyclooctadiene lignans interiotherin A, angeloylgomisin R, gomisin O, and gomisin E (epigomisin O) are presented. The syntheses were based on a unified synthetic strategy involving a novel crotylation using the Leighton auxiliary that occurred with excellent asymmetric induction (>98:2 enantiomeric ratio), a diastereoselective hydroboration/Suzuki-Miyaura coupling reaction sequence, and an atropdiastereoselective biarylcuprate coupling, both of which occurred with total (>20:1) stereocontrol. The syntheses were achieved in six to eight steps from simple aromatic precursors.
Coleman
Robert S
RS
Department of Chemistry, The Ohio State University, Columbus, 43210, USA. coleman@chemistry.ohio-state.edu
Gurrala
Srinivas Reddy
SR
Mitra
Soumya
S
Raao
Amresh
A
D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001888:Boric Acids / Q000737:chemistry; D002073:Butanes / Q000737:chemistry; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000447:Aldehydes; D001688:Biological Products; D001888:Boric Acids; D002073:Butanes; D034242:Cyclooctanes; D017705:Lignans; C510994:dibenzocyclooctadiene lignan; C046888:butane; D006859:Hydrogen; C032688:boric acid