Enantioselective Synthesis of Paraconic Acids
- 30 December 2002
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (1) , 260-270
- https://doi.org/10.1002/chem.200390019
Abstract
The development of a new method for the enantioselective synthesis of disubstituted γ-butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (−)-roccellaric acid, (−)-nephrosteranic acid and (−)-protopraesorediosic acid, and the formal total synthesis of (−)-methylenolactocin and (−)-protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper(I)-catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium(II)-catalyzed, intermolecular cross metathesis reactions.Keywords
This publication has 98 references indexed in Scilit:
- Enantioselektive Synthese mit Lithium/(−)‐Spartein‐Carbanion‐PaarenAngewandte Chemie, 1997
- Olefin Cross‐Metathesis with Monosubstituted OlefinsChemistry – A European Journal, 1997
- Regio‐ und stereokontrollierte konjugierte Radikaladdition an ein asymmetrisches Fumarsäure‐Derivat‐effiziente Synthese von (−)‐Nephrosteran‐ und (−)‐RoccellarinsäureAngewandte Chemie, 1997
- Electrophilic .gamma.-lactone .kappa.-opioid receptor probes. Analogs of 2'-hydroxy-2-(tetrahydrofurfuryl)-5,9-dimethyl-6,7-benzomorphan diastereomersJournal of Medicinal Chemistry, 1991
- Asymmetrische Homoaldol‐Reaktion durch enantioselektive Lithiierung eines prochiralen 2‐ButenylcarbamatsAngewandte Chemie, 1989
- Asymmetric Homoaldol Reaction by Enantioselective Lithiation of a Prochiral 2‐Butenyl CarbamateAngewandte Chemie International Edition in English, 1989
- The Homoaldol Reaction, or How to Overcome Problems of Regio‐ and Stereo‐selectivityAngewandte Chemie International Edition in English, 1984
- Die Homoaldol-Reaktion oder wie man Probleme der Regio- und Stereoselektivität in den Griff bekommtAngewandte Chemie, 1984
- An effective approach to stereocontrolled lactone annulation. Application to the total synthesis of pentalenolactone E methyl ester and a partial elaboration of quadroneJournal of the American Chemical Society, 1982
- The Synthesis of dl-Protolichesterinic Acid1Journal of the American Chemical Society, 1958