To create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. Total synthesis and absolute stereochemistry of (+)batzellaside B and its C8-epimer, a new class of piperidine alkaloids from the sponge Batzella sp.
The first stereoselective synthesis of penicillenol A 1 has been accomplished in nine steps from L-threonine. The 3-acyltetramic acid core of penicillenol A 1 was constructed by successful Oto C-acyl rearrangement.
SummaryA new synthetic approach to (+)-batzellaside B from naturally abundant L-pyroglutamic acid is presented in this article. The key synthetic step involves Sharpless asymmetric dihydroxylation of an olefinic substrate functionalized with an acetoxy group to introduce two chiral centres diastereoselectively into the structure. Heterocyclic hemiaminal 4, which could be converted from the resulting product, was found to provide stereospecific access to enantiomerically enriched allylated intermediate, offering better prospects for the total synthesis of this natural product.
Total Synthesis and Absolute Stereochemistry of (+)-Batzellaside B (I) and Its C8-Epimer, a New Class of Piperidine Alkaloids from the Sponge Batzella sp. -(WIERZEJSKA, J.; OHSHIMA, M.; INUZUKA, T.; SENGOKU, T.; TAKAHASHI, M.; YODA*, H.; Tetrahedron Lett. 52 (2011) 11, 1173-1175, http://dx.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.