Toward the Combinatorial Synthesis of Polyketide Libraries: Asymmetric Aldol Reactions with α-Chiral Aldehydes on Solid Support
- 22 June 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (15) , 2473-2476
- https://doi.org/10.1021/ol026046+
Abstract
The viability of performing stereocontrolled aldol additions with α-chiral aldehydes attached by a silyl linker to a hydroxymethylpolystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipulation on the solid support leads to elaborate stereopentad sequences, as occur in 6-deoxyerythronolide B and discodermolide.Keywords
This publication has 28 references indexed in Scilit:
- Glossary of Terms Used in Combinatorial Chemistry (Technical Report)Journal of Combinatorial Chemistry, 2000
- A Combinatorial Approach to Polyketide-Type Libraries by Iterative Asymmetric Aldol Reactions Performed on Solid SupportPublished by Wiley ,2000
- A New Polymer Support Silylene Linking Method for Hindered Hydroxyl-Bearing SystemsThe Journal of Organic Chemistry, 1999
- Laboratory emulation of polyketide biosynthesis: an iterative, aldol-based, synthetic entry to polyketide libraries using (R)- and (S )-1-(benzyloxy)-2-methylpentan-3-one, and conformational aspects of extended polypropionatesJournal of the Chemical Society, Perkin Transactions 1, 1999
- (+)-Discodermolide binds to microtubules in stoichiometric ratio to tubulin dimers, blocks taxol binding and results in mitotic arrestChemistry & Biology, 1996
- Discodermolide, A Cytotoxic Marine Agent That Stabilizes Microtubules More Potently Than Taxol,Biochemistry, 1996
- Biosynthesis of fatty acid and polyketide metabolitesNatural Product Reports, 1995
- Studies in Macrolide Synthesis: A Stereocontrolled Synthesis of Oleandolide Employing Reagent- and Substrate-Controlled Aldol Reactions of (S)-1-(Benzyloxy)-2-methylpentan-3-oneJournal of the American Chemical Society, 1994
- Stereoselective aldol reactions of chlorotitanium enolates. An efficient method for the assemblage of polypropionate-related synthonsJournal of the American Chemical Society, 1991
- Samarium-catalyzed intramolecular Tishchenko reduction of .beta.-hydroxy ketones. A stereoselective approach to the synthesis of differentiated anti 1,3-diol monoestersJournal of the American Chemical Society, 1990