Total Synthesis of a 28-Member Stereoisomer Library of Murisolins
- 28 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (29) , 9561-9573
- https://doi.org/10.1021/ja061801q
Abstract
Total syntheses of two 16-member libraries of murisolin isomers are reported. In the first library, fluorous PMB (p-methoxybenzyl) groups encode configurations, and four mixtures of four dihydroxy-tetrahydrofurans are prepared by Shi epoxidation followed (optionally) by Mitsunobu reaction. The mixtures are coupled by Kocienski−Julia reaction with a single hydroxybutenolide followed by hydrogenation. Demixing and detagging provide the 16 pure stereoisomers. In the second synthesis, a single mixture of four fluorous-tagged dihydroxy-tetrahydrofurans is coupled with a four-compound mixture of hydroxybutenolides that bear derivatives of DMB (dimethoxybenzyl) groups with oligoethylene glycol (OEG) units that encode the configurations at C4 and C34. The 16-compound mixture is subjected to hydrogenation, double demixing, and detagging to provide the 16 isomerically pure murisolins. Twelve of these isomers are new, while four match samples from the first library.Keywords
This publication has 20 references indexed in Scilit:
- Solution-Phase Mixture Synthesis with Double-Separation Tagging: Double Demixing of a Single Mixture Provides a Stereoisomer Library of 16 Individual MurisolinsAngewandte Chemie International Edition in English, 2005
- Total Synthesis of Murisolins and Evaluation of Tumor‐Growth Inhibitory ActivityChemistry – A European Journal, 2005
- Fluorous Mixture Synthesis of Fused-Tricyclic Hydantoins. Use of a Redundant Tagging Strategy on Fluorinated SubstratesThe Journal of Organic Chemistry, 2005
- Fluorous Mixture Synthesis of 4-Alkylidene Cyclopentenones via a Rhodium-Catalyzed [2+2+1] Cycloaddition of Alkynyl AllenesJournal of Combinatorial Chemistry, 2004
- Systematic Construction of a Monotetrahydrofuran‐Ring Library in Annonaceous Acetogenins by Asymmetric Alkynylation and Stereodivergent Tetrahydrofuran‐Ring FormationChemistry – A European Journal, 2003
- Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)CoIIIComplexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-DiolsJournal of the American Chemical Society, 2002
- Reversible Surface Morphology Changes of a Photochromic Diarylethene Single Crystal by PhotoirradiationScience, 2001
- Dibutyltin Oxide Catalyzed Selective Sulfonylation of α-Chelatable Primary AlcoholsOrganic Letters, 1999
- Toward Chemical Libraries of Annonaceous Acetogenins. Total Synthesis of TrilobacinThe Journal of Organic Chemistry, 1996
- Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excessThe Journal of Organic Chemistry, 1986