Fluorous Mixture Synthesis of Stereoisomer Libraries: Total Syntheses of (+)-Murisolin and Fifteen Diastereoisomers
- 10 December 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (1) , 36-37
- https://doi.org/10.1021/ja038542e
Abstract
The synthesis of a stereoisomer library of 16 murisolins in individual pure form by fluorous mixture synthesis is reported. Four stereoisomeric precursors are tagged with different fluorous tags, and the resulting mixture is taken through the synthesis with four splits and late stage demixing and detagging to give all 16 products. These products exhibit only six different sets of NMR spectra, but all can be differentiated by chiral HPLC. The structure of murisolin is confirmed, but the structures of murisolin A and 16,19-cis-murisolin may never be known with certainty because insufficient data were collected on natural samples to differentiate each of them from one other isomer.Keywords
This publication has 10 references indexed in Scilit:
- NMR Determination of Absolute Configuration of Butenolides of Annonaceous TypeChemistry – A European Journal, 2002
- Thiol additions to acrylates by fluorous mixture synthesis: relative control of elution order in demixing by the fluorous tag and the thiol substituentTetrahedron, 2001
- Reversible Surface Morphology Changes of a Photochromic Diarylethene Single Crystal by PhotoirradiationScience, 2001
- Total Synthesis of Asimicin and BullatacinThe Journal of Organic Chemistry, 2000
- Gram-Scale Synthesis of (+)-DiscodermolideOrganic Letters, 1999
- Determination of Absolute Configurations of Carbinols of Annonaceous Acetogenins with 2-Naphthylmethoxyacetic Acid EstersThe Journal of Organic Chemistry, 1998
- An Efficient Catalytic Asymmetric Epoxidation MethodJournal of the American Chemical Society, 1997
- Transition-metal-promoted reactions. 25. Regioselective silylolefination of allylic dithioacetals. Stereoselective synthesis of 1-(trimethylsilyl)butadienesThe Journal of Organic Chemistry, 1988
- Chiral synthesis via organoboranes. 13. A highly diastereoselective and enantioselective addition of [(Z)-.gamma.-alkoxyallyl]diisopinocampheylboranes to aldehydesJournal of the American Chemical Society, 1988
- Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excessThe Journal of Organic Chemistry, 1986