1178869-99-2Relevant academic research and scientific papers
(+)-Rimocidin synthetic studies: Construction of the C(1-27) aglycone skeleton
Smith III, Amos B.,Foley, Megan A.,Dong, Shuzhi,Orbin, Alia
supporting information; experimental part, p. 5987 - 6001 (2009/12/26)
(Chemical Equation Presented) Assembly of the C(1-27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the SN2/SN2′ reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1-19) carbon backbone. Yamaguchi union of a C(20-27) vinyl borate ester, possessing the all-trans triene, with an advanced C(1-19) vinyl iodide followed by macrocyclization via Suzuki-Miyaura crosscoupling completed construction of the C(1-27) rimocidinolide skeleton.
