Enantiospecific synthesis of (+)-and (–)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine
M Nambu, JD White
文献索引:Nambu, Mitch; White, James D. Chemical Communications, 1996 , # 14 p. 1619 - 1620
Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-α and AD-mix- β, followed by saponification, gives (–)-and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.
[Beddow, James E.; Davies, Stephen G.; Ling, Kenneth B.; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Thomson, James E. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 17 p. 2812 - 2825]