Synthesis of (−)‐Berkelic Acid
- 28 January 2009
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 48 (7), 1283-1286
- https://doi.org/10.1002/anie.200805488
Abstract
An extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6‐dihydroxybenzoic acid is the key step in the synthesis of (−)‐berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.Keywords
This publication has 25 references indexed in Scilit:
- A Synthesis‐Driven Structure Revision of Berkelic Acid Methyl EsterAngewandte Chemie, 2008
- A Cycloaddition Strategy for Use toward Berkelic Acid, an MMP Inhibitor and Potent Anticancer Agent Displaying a Unique Chroman Spiroketal MotifSynlett, 2008
- Diastereoselective Syntheses of Chroman Spiroketals via [4 + 2] Cycloaddition of Enol Ethers and o-Quinone MethidesOrganic Letters, 2008
- Biomimetic Synthesis of the Tetracyclic Core of Berkelic AcidOrganic Letters, 2007
- Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: the effect of heteroatom and substitution pattern on phase stabilityJournal of Materials Chemistry, 2007
- Regulated-Stereoselective Construction of Thirteen Stereogenic Centers Necessary for the Frame of (+)-Discodermolide, Based on Iterative Lewis Acid-Promoted Aldol ReactionsThe Journal of Organic Chemistry, 2003
- A Mild, Efficient and Selective Cleavage of Aryl tert-Butyldimethysilyl Ethers Using KOH in EthanolChemistry Letters, 2003
- Asymmetric Conjugate Additions of Chiral Phosphonamide Anions to α,β-Unsaturated Carbonyl Compounds. A Versatile Method for Vicinally Substituted ChironsThe Journal of Organic Chemistry, 2000
- Enantioselective chiral borane-mediated aldol reactions of silyl ketene acetals with aldehydes. The novel effect of the trialkysilyl group of the silyl ketene acetal on the reaction courseThe Journal of Organic Chemistry, 1991
- The synthesis of (±)-pulvilloric acid and of (±) methyl dihydropul-villorateJournal of the Chemical Society C: Organic, 1967