Enantioselective Total Synthesis of (+)-Salvileucalin B
- 21 December 2010
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (4), 774-776
- https://doi.org/10.1021/ja110192b
Abstract
An enantioselective total synthesis of the diterpenoid natural product (+)-salvileucalin B is reported. Key findings include a copper-catalyzed arene cyclopropanation reaction to provide the unusual norcaradiene core and a reversible retro-Claisen rearrangement of a highly functionalized norcaradiene intermediate.Keywords
This publication has 21 references indexed in Scilit:
- How an Enzyme Might Accelerate an Intramolecular Diels−Alder Reaction: Theozymes for the Formation of Salvileucalin BOrganic Letters, 2010
- Salvileucalin B, A Novel Diterpenoid with an Unprecedented Rearranged Neoclerodane Skeleton from Salvia leucantha Cav.Organic Letters, 2008
- Stereoselective Cyclopropanation ReactionsChemical Reviews, 2003
- Synthesis of cyclopropane containing natural productsTetrahedron, 2001
- Enantioselective Synthesis of Fused Cycloheptadienes by a Tandem Intramolecular Cyclopropanation/Cope Rearrangement SequenceThe Journal of Organic Chemistry, 1999
- Norcaradienes from the Intramolecular Cyclopropanation Reactions of Diazomethyl Ketones. Valuable Intermediates for the Synthesis of Polycyclic DiterpenesSynthesis, 1998
- A New and Efficient Strategy for the Total Synthesis of Polycyclic Diterpenoids: The Preparation of Gibberellins (±)-GA103 and (±)-GA73Journal of the American Chemical Society, 1997
- Ligand Effects on the Chemoselectivity of Transition Metal Catalyzed Reactions of α‐Diazo Carbonyl CompoundsAngewandte Chemie-International Edition, 1994
- General Methodology for the Topologically Selective Preparation of Linear and Nonlinear Tricyclopentanoids of Hirsutane and Isocomene Typeviaa Claisen Rearrangement / Cyclopentene Annulation Sequence. Total Synthesis of (±)- EpiisocomeneSynthesis, 1986
- Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum(Labiatae)Journal of the Chemical Society, Perkin Transactions 1, 1982