Back to Search
Start Over
Microwave-enhanced, stereospecific ring-closure of medium-ring cyanamide ethers to yohimbine
- Source :
- Tetrahedron Letters. 60:1182-1185
- Publication Year :
- 2019
- Publisher :
- Elsevier BV, 2019.
-
Abstract
- A highly efficient acid-promoted, stereospecific, transannular ring-closure of medium-ring ether compounds to the indole alkaloid yohimbine is described. Microwave-enhanced acetic acid degradation of cyanamide compounds involves loss of (R)- or (S)-ethers, followed by a stereospecific, nucleophilic ring-closure from the cyanamide to afford yohimbine in up to 74% yield in as little as one minute. This nucleophilic reactivity of the amino moiety of the cyanamide highlights an alternative reactivity profile from its traditional electrophilic properties. Additionally, this reaction pathway highlights a rare case of an SN1 pathway that proceeds with complete stereospecificity.
- Subjects :
- Indole alkaloid
010405 organic chemistry
Organic Chemistry
Ether
010402 general chemistry
01 natural sciences
Biochemistry
Medicinal chemistry
0104 chemical sciences
chemistry.chemical_compound
Stereospecificity
chemistry
Nucleophile
Drug Discovery
Electrophile
Moiety
Cyanamide
Reactivity (chemistry)
Subjects
Details
- ISSN :
- 00404039
- Volume :
- 60
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi...........1b9843bfdc5ddd0cccafb4854d04f798