Tackling reactivity and selectivity within a strained architecture: construction of the [6-6-5-7] tetracyclic core of Calyciphylline alkaloids.

Autor: Xu C; Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen University Town, Nanshan District, Shenzhen 518055, China., Wang L, Hao X, Wang DZ
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2012 Jul 20; Vol. 77 (14), pp. 6307-13. Date of Electronic Publication: 2012 Jul 03.
DOI: 10.1021/jo300776d
Abstrakt: A stereochemically controlled route to the enantiopure [6-6-5-7] tetracyclic core of Calyciphylline A class alkaloids was established, which involves Overman rearrangement, [2 + 2] photochemical cycloaddition, Grob fragmentation, C-N bond-forming nucleophilic displacement, and ring strain-directed hydrogenation as strategic steps.
Databáze: MEDLINE