Ontology highlight
ABSTRACT:
SUBMITTER: Tsukanov SV
PROVIDER: S-EPMC4184464 | biostudies-literature | 2014 Oct
REPOSITORIES: biostudies-literature
Tsukanov Sergey V SV Comins Daniel L DL
The Journal of organic chemistry 20140917 19
Concise and highly stereocontrolled total syntheses of racemic and enantiopure frog alkaloid 205B (1) were accomplished in 11 steps from 4-methoxypyridines 6 and 7 in overall yields of 8 and 8%, respectively. The assembly of the core of the natural product relies on a stereoselective Tsuji-Trost allylic amination reaction and a ring-closing metathesis. The synthesis features the use of an N-acylpyridinium salt reaction to introduce the first stereocenter and an unprecedented trifluoroacetic anhy ...[more]