Journal article
Application of the Nickel-Mediated Neopentyl Coupling in the Total Synthesis of the Marine Natural Product Arenarol
Journal of organic chemistry, Vol.60(16), pp.5102-5106
08/01/1995
DOI: 10.1021/jo00121a030
Abstract
Racemic arenarol (1) has been synthesized from the known decalin 5β-carbethoxy-1,1-(1,2-ethylenedioxy)-5α,8aβ-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-oxonaphthalene (9) via a short, efficient, and highly stereocontrolled sequence. Key steps in this synthesis are the directed hydrogenation of an unsaturated neopentyl alcohol to provide stereocontrolled formation of the two adjacent tertiary centers and subsequent elaboration of the arenarol skeleton via a nickel-mediated coupling of the corresponding neopentyl iodide. This sequence demonstrates the value of nickel-mediated crosscoupling reactions for carbon-carbon bond formation at neopentyl centers. © 1995, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Application of the Nickel-Mediated Neopentyl Coupling in the Total Synthesis of the Marine Natural Product Arenarol
- Creators
- Anthony T WatsonKwangyong ParkDavid F WiemerWilliam J Scott
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.60(16), pp.5102-5106
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00121a030
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 08/01/1995
- Academic Unit
- Chemistry; Neuroscience and Pharmacology
- Record Identifier
- 9984216582102771
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