116005-49-3Relevant academic research and scientific papers
The cascade radical cyclisation approach to prenylated alkaloids: Synthesis of stephacidin A and notoamide B
Simpkins, Nigel S.,Pavlakos, Ilias,Weller, Michael D.,Male, Louise
, p. 4957 - 4970 (2013/08/23)
A strategy for the synthesis of members of the prenylated indole alkaloid family is described, which involves a radical cascade process of an appropriately substituted diketopiperazine (DKP) core structure. Several approaches to the generation of the initial radical were explored, with the most successful involving treatment of a sulfenyl substituted DKP under classical reductive conditions by heating with Bu3SnH and a radical initiator. The required, fully substituted, radical precursor DKP structures were prepared using regio- and stereocontrolled enolate chemistry of simpler proline-tryptophan derived DKPs. The new approach allowed rapid access to a key polycyclic indoline structure, which was converted into either of the natural products stephacidin A or notoamide B.
Enantioselective total synthesis of avrainvillamide and the stephacidins
Baran, Phil S.,Hafensteiner, Benjamin D.,Ambhaikar, Narendra B.,Guerrero, Carlos A.,Gallagher, John D.
, p. 8678 - 8693 (2007/10/03)
In this article, full details regarding our total synthesis of avrainvillamide and the stephacidins are presented. After an introduction and summary of prior synthetic studies in this family of structurally complex anticancer natural products, the evoluti
Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B
Williams, Robert M.,Glinka, Tomasz,Kwast, Ewa,Coffman, Hazel,Stille, James K.
, p. 808 - 821 (2007/10/02)
The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular SN2′ cyclization to construct the central bicyclo[2.2.2] nucleus. A synthetic route to C-10-epibre
