Total Synthesis of (−)-Pseudolaric Acid B
- 7 November 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (47), 14556-14557
- https://doi.org/10.1021/ja076165q
Abstract
We report the enantioselective synthesis of pseudolaric acid B (1a), a diterpene acid isolated from the bark of Pseudolarix kaempferi Gordon, which displays interesting antifungal, antifertility, and cytotoxic activity against multidrug resistant cell lines. Our synthesis utilizes a highly efficient metal-catalyzed [5 + 2] vinylcyclopropane-alkyne intramolecular cycloaddition to construct the polyhydroazulene core of the natural product. Elaboration to the tricyclic scaffold of the pseudolaric acids was completed with an intramolecular alkoxycarbonyl radical cyclization to form the quaternary center and a highly diastereoselective cerium acetylide addition to a methyl ketone for introduction of the acid side chain.This publication has 21 references indexed in Scilit:
- Total Synthesis of Pseudolaric Acid AAngewandte Chemie, 2006
- Soluble Lanthanide Salts (LnCl3⋅2 LiCl) for the Improved Addition of Organomagnesium Reagents to Carbonyl CompoundsAngewandte Chemie, 2006
- Pseudolaric Acid B, a Novel Microtubule-Destabilizing Agent That Circumvents Multidrug Resistance Phenotype and Exhibits Antitumor Activity In vivoClinical Cancer Research, 2005
- Syntheses of Seven-Membered Rings: Ruthenium-Catalyzed Intramolecular [5+2] CycloadditionsChemistry – A European Journal, 2005
- [(arene)Rh(cod)] Complexes as Catalysts for [5+2] Cycloaddition ReactionsAngewandte Chemie, 2002
- Enantioselective Cyclopropanation of Allylic Alcohols with Dioxaborolane Ligands: Scope and Synthetic ApplicationsJournal of the American Chemical Society, 1998
- Transition Metal Catalyzed [5 + 2] Cycloadditions of Vinylcyclopropanes and Alkynes: A Homolog of the Diels-Alder Reaction for the Synthesis of Seven-Membered RingsJournal of the American Chemical Society, 1995
- Total synthesis of (+)-macbecin IJournal of the Chemical Society, Perkin Transactions 1, 1990
- Pseudolaric acid B: NMR assignments, conformational analysis and cytotoxicityMagnetic Resonance in Chemistry, 1989
- Total synthesis of (.+-.)-atractyligeninJournal of the American Chemical Society, 1987