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Divergent total synthesis of the Lycopodium alkaloids huperzine A, huperzine B, and huperzine U.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2014 Jan 03; Vol. 79 (1), pp. 240-50. Date of Electronic Publication: 2013 Dec 10. - Publication Year :
- 2014
-
Abstract
- Huperzine A, huperzine B, and huperzine U are congeners isolated from the Chinese herb Huperzia serrata (= Lycopodium serratum ) in minuscule amounts. The most efficient total synthesis of huperzine A, the first asymmetric total syntheses of huperzine B, and the first total synthesis of huperzine U have been achieved efficiently in overall yields of 17%, 10%, and 9%, respectively, each spanning 10-13 steps from (R)-pulegone. The featured steps include palladium-catalyzed Buchwald-Hartwig coupling and Heck cyclization reactions and an Ir-catalyzed olefin isomerization reaction. This work has established the absolute configurations of huperzine B and huperzine U and revealed that natural huperzine A, huperzine B, and huperzine U possess the same set of absolute stereochemistries, thus providing support for the potential role of huperzine B and huperzine U in the biosynthesis of huperzine A.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 79
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24299147
- Full Text :
- https://doi.org/10.1021/jo402419h