852123-22-9Relevant articles and documents
Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products
Coleman, Robert S.,Gurrala, Srinivas Reddy,Mitra, Soumya,Raao, Amresh
, p. 8932 - 8941 (2007/10/03)
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.