Enantioselective synthesis of a taxol C ring
- 23 December 2011
- journal article
- research article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 76 (12), 1579-1594
- https://doi.org/10.1135/cccc2011039
Abstract
An enantioselective synthesis of a C ring of taxol has been accomplished. The key step is an oxidative cleavage of a derivative of the Wieland–Miescher ketone. A first attempt of a Shapiro reaction modelling the coupling of the C ring with the A fragment of taxol was also successful.Keywords
This publication has 43 references indexed in Scilit:
- Ring‐Closing Metathesis in the Synthesis of BC Ring‐Systems of TaxolChemistry – A European Journal, 2008
- A Formal Total Synthesis of Taxol Aided by an Automated SynthesizerChemistry – An Asian Journal, 2006
- Diastereoselective Synthesis of a seco-TaxaneSynlett, 1999
- A Unified Strategy for the Stereocontrolled Construction of Structurally Unusual Sesquiterpene Lactones. Asymmetric Synthesis of Vulgarolide and DeoxocrispolideJournal of the American Chemical Society, 1996
- Studies on the Biosynthesis of Taxol: Total Synthesis of Taxa-4(20),11(12)-diene and Taxa-4(5),11(12)-diene. The First Committed Biosynthetic IntermediateThe Journal of Organic Chemistry, 1995
- Stereoselective construction of the taxinine AB system through a novel tandem aldol-Payne rearrangement annulationThe Journal of Organic Chemistry, 1990
- A synthesis of an alkylated taxane model systemJournal of the Chemical Society, Perkin Transactions 1, 1989
- A new synthesis of substituted dienes and its application to an alkylated taxane model systemJournal of the Chemical Society, Chemical Communications, 1987
- Synthesis of the taxane ring system using an intramolecular Diels–Alder reaction of a 2-substituted dieneJournal of the Chemical Society, Perkin Transactions 1, 1986
- A stereocontrolled route to the tricyclo[9.3.1.03,8]pentadecane ring system of taxaneJournal of the Chemical Society, Chemical Communications, 1984