Total synthesis of himandravine.
Publication
, Journal Article
Chackalamannil, S; Davies, R; McPhail, AT
Published in: Organic letters
May 2001
[reaction: see text] The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular Diels-Alder reaction of the key intermediate 5 that contains the entire latent carbon framework and functional group substitution of himandravine.
Duke Scholars
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
May 2001
Volume
3
Issue
10
Start / End Page
1427 / 1429
Related Subject Headings
- Stereoisomerism
- Plant Extracts
- Piperidines
- Organic Chemistry
- Alkaloids
- 34 Chemical sciences
- 03 Chemical Sciences
Citation
APA
Chicago
ICMJE
MLA
NLM
Chackalamannil, S., Davies, R., & McPhail, A. T. (2001). Total synthesis of himandravine. Organic Letters, 3(10), 1427–1429. https://doi.org/10.1021/ol010038w
Chackalamannil, S., R. Davies, and A. T. McPhail. “Total synthesis of himandravine.” Organic Letters 3, no. 10 (May 2001): 1427–29. https://doi.org/10.1021/ol010038w.
Chackalamannil S, Davies R, McPhail AT. Total synthesis of himandravine. Organic letters. 2001 May;3(10):1427–9.
Chackalamannil, S., et al. “Total synthesis of himandravine.” Organic Letters, vol. 3, no. 10, May 2001, pp. 1427–29. Epmc, doi:10.1021/ol010038w.
Chackalamannil S, Davies R, McPhail AT. Total synthesis of himandravine. Organic letters. 2001 May;3(10):1427–1429.
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
May 2001
Volume
3
Issue
10
Start / End Page
1427 / 1429
Related Subject Headings
- Stereoisomerism
- Plant Extracts
- Piperidines
- Organic Chemistry
- Alkaloids
- 34 Chemical sciences
- 03 Chemical Sciences