Total Synthesis of (−)-Apicularen A
- 4 February 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (8) , 2425-2430
- https://doi.org/10.1021/ja037957x
Abstract
Complete details of an asymmetric synthesis of apicularen (1) are described. The synthesis has been accomplished using a highly diastereo- and enantioselective [4 + 2] annulation for the assembly of the functionalized pyran core. An underdeveloped lactonization method involving an NaH promoted transesterification of an advanced intermediate bearing an aryl cyanomethyl ester was used for the macrolactonization step.Keywords
This publication has 25 references indexed in Scilit:
- Stereochemistry of Nucleophilic Substitution Reactions Depending upon Substituent: Evidence for Electrostatic Stabilization of Pseudoaxial Conformers of Oxocarbenium Ions by Heteroatom SubstituentsJournal of the American Chemical Society, 2003
- Lobatamide C: Total Synthesis, Stereochemical Assignment, Preparation of Simplified Analogues, and V-ATPase Inhibition StudiesJournal of the American Chemical Society, 2003
- Stereoselective Synthesis of Functonalized Dihydropyrans via a Formal [4+2]-Annulation of Chiral CrotylsilanesJournal of the American Chemical Society, 2000
- Stereoselective Synthesis of the Chiral Tetrahydropyrane Core of Swinholides and MisakinolidesChemistry Letters, 1999
- Cyanomethyl Esters: Useful Protection for Carboxylic AcidsSynthetic Communications, 1992
- Synthesis of (.+-.)cervinomycins A1 and A2Journal of the American Chemical Society, 1989
- Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatizationJournal of the American Chemical Society, 1987
- Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excessThe Journal of Organic Chemistry, 1986
- The Oxymercuration-Demercuration of Representative Olefins. A Convenient, Mild Procedure for the Markovnikov Hydration of the Carbon-Carbon Double BondJournal of the American Chemical Society, 1967
- A STEREOSPECIFIC CIS HYDRATION OF THE DOUBLE BOND IN CYCLIC DERIVATIVESJournal of the American Chemical Society, 1959