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Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis.
- Source :
-
Chemistry - An Asian Journal . May2016, Vol. 11 Issue 9, p1425-1435. 11p. - Publication Year :
- 2016
-
Abstract
- Two independent synthetic approaches were evaluated for the final phase of the asymmetric total synthesis of propindilactone G ( 1). The key steps that led to the completion of the asymmetric total synthesis included: 1) an intermolecular oxidative heterocoupling reaction of enolsilanes to link the core structure to the side chain; 2) an intermolecular Wittig reaction for the formation of the α,β,γ,δ-unsaturated ester; and 3) a regio- and stereoselective OsO4-catalyzed dihydroxylation of an α,β,γ,δ-unsaturated enone, followed by an intramolecular lactonization reaction to afford the final product. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised. Furthermore, the direct oxidative coupling strategy for ligation of the core of propindilactone G with its side chain may find application in the syntheses of other natural products and complex molecules. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 18614728
- Volume :
- 11
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Chemistry - An Asian Journal
- Publication Type :
- Academic Journal
- Accession number :
- 115247692
- Full Text :
- https://doi.org/10.1002/asia.201600131