Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one
Publication
, Journal Article
Armstrong, P; O'Mahony, G; Stevenson, PJ; Walker, AD
Published in: Tetrahedron Letters
November 21, 2005
Catalytic hydrogenation of dihydroindolizidinone occurred preferentially from the endo-face giving rapid entry to (8R,8aS)-8-methylhexahydroindolizin-5- one, a key intermediate in the synthesis of 5,8-disubstituted indolizidines and deoxypumiliotoxin 251H. The selectivity could be improved further by diimide reduction though this also resulted in some oxidation of the alkene to the diene. The basis of the unusual stereoselectivity in the diimide reduction is believed to be stereoelectronic in origin. © 2005 Elsevier Ltd. All rights reserved.
Duke Scholars
Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
November 21, 2005
Volume
46
Issue
47
Start / End Page
8109 / 8111
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Armstrong, P., O’Mahony, G., Stevenson, P. J., & Walker, A. D. (2005). Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one. Tetrahedron Letters, 46(47), 8109–8111. https://doi.org/10.1016/j.tetlet.2005.09.133
Armstrong, P., G. O’Mahony, P. J. Stevenson, and A. D. Walker. “Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one.” Tetrahedron Letters 46, no. 47 (November 21, 2005): 8109–11. https://doi.org/10.1016/j.tetlet.2005.09.133.
Armstrong P, O’Mahony G, Stevenson PJ, Walker AD. Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one. Tetrahedron Letters. 2005 Nov 21;46(47):8109–11.
Armstrong, P., et al. “Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one.” Tetrahedron Letters, vol. 46, no. 47, Nov. 2005, pp. 8109–11. Scopus, doi:10.1016/j.tetlet.2005.09.133.
Armstrong P, O’Mahony G, Stevenson PJ, Walker AD. Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one. Tetrahedron Letters. 2005 Nov 21;46(47):8109–8111.
Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
November 21, 2005
Volume
46
Issue
47
Start / End Page
8109 / 8111
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry