Asymmetric Total Synthesis of Dibenzocyclooctadiene Lignan Natural Products
- 1 October 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (22) , 8932-8941
Abstract
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.Keywords
This publication has 85 references indexed in Scilit:
- A Highly Practical and Enantioselective Reagent for the Allylation of AldehydesAngewandte Chemie International Edition, 2003
- Catalytic enantioselective allylation of ketones with novel chiral bis‐titanium(IV) catalystChirality, 2002
- The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product SynthesisAngewandte Chemie International Edition, 2001
- New Chiral Bis-Titanium(IV) Catalyst with Dibenzofuran Spacer for Catalytic Asymmetric Allylation of Aldehydes and Aryl KetonesAdvanced Synthesis & Catalysis, 2001
- On the Constitutional Stability ofη1-Allylmetal CompoundsChemistry – A European Journal, 1998
- Asymmetric Synthesis of Biaryls by Intramolecular Oxidative Couplings of Cyanocuprate IntermediatesAngewandte Chemie International Edition, 1994
- Diastereogenic Addition of Crotylmetal Compounds to AldehydesAngewandte Chemie International Edition, 1982
- Capricious Stereoselectivities of Alkenylpotassium Formation under Kinetic and Thermodynamic Control Oxygen‐Triggered Configurational Equilibration of an Allyl Type Organometallic CompoundHelvetica Chimica Acta, 1977
- Prescriptions and Ingredients for Controlled CC Bond Formation with Organometallic Reagents. New synthetic methods (5)Angewandte Chemie International Edition, 1974
- Selektive Synthesen mit Organometallen I. Konfigurativ einheitliche Folgeprodukte aus Alkenylkalium‐ZwischenstufenHelvetica Chimica Acta, 1974