Journal article
Total synthesis of (+)-jatrophone
Journal of the American Chemical Society, Vol.114(20), pp.7692-7697
09/01/1992
DOI: 10.1021/ja00046a014
Abstract
The first total synthesis of optically active (+)-jatrophone is described. A convergent sequence provides the natural enantiomer in just 12 steps from (/?)-(+)-3-methyladipic acid. Key steps include formation of the jatrophone C-ring through a Wadsworth-Homer-Emmons variant, a Pd-catalyzed cross-coupling that incorporates the C5-C6 double bond with the required Z-stereochemistry, and formation of the macrocycle by condensation of an acetylenic aldehyde. This sequence provides a short, efficient, and stereocontrolled route to the complex diterpenoid (+)-jatrophon
Details
- Title: Subtitle
- Total synthesis of (+)-jatrophone
- Creators
- Qi HanDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of the American Chemical Society, Vol.114(20), pp.7692-7697
- Publisher
- American Chemical Society
- DOI
- 10.1021/ja00046a014
- ISSN
- 0002-7863
- eISSN
- 1520-5126
- Language
- English
- Date published
- 09/01/1992
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985825302771
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