Journal article
Stereoselective Synthesis of (+)-Avarol, (+)-Avarone, and Some Nonracemic Analogues
Journal of organic chemistry, Vol.61(25), pp.8775-8779
12/13/1996
DOI: 10.1021/jo961048r
PMID: 11667853
Abstract
Synthesis of the rearranged drimane sesquiterpenoids (+)-avarol and (+)-avarone from Wieland−Miescher ketone is described. This synthetic sequence provides convenient access to the natural enantiomers and, based on comparison of the optical rotation of synthetic avarol dimethyl ether with literature data, affords material of significantly higher optical rotation than a natural source. Similar synthetic strategies have been used to obtain several related compounds, including a decalin bearing an exocyclic olefin and a highly substituted cyclohexane, that can be viewed as hybrids of the trans-fused avarol and cis-fused arenarol skeletons.
Details
- Title: Subtitle
- Stereoselective Synthesis of (+)-Avarol, (+)-Avarone, and Some Nonracemic Analogues
- Creators
- Jianguo AnDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.61(25), pp.8775-8779
- DOI
- 10.1021/jo961048r
- PMID
- 11667853
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society
- Language
- English
- Date published
- 12/13/1996
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985856502771
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