701211-87-2Relevant academic research and scientific papers
Studies directed toward the synthesis of the massileunicellins. Part 2
Chai, Yonghai,Mou, Zonghong,McIntosh, Matthias C.
supporting information; experimental part, p. 2393 - 2395 (2010/06/21)
The fully substituted hydroisobenzofuran core of the massileunicellins containing eight contiguous stereocenters was prepared in 12 steps from (S)-(+)-carvone. Noteworthy elements of the synthesis include a one-step oxidative rearrangement/epoxidation, a novel stereoselective directed reduction of a keto diol, and a directed hydrogenation of a congested tetrasubstituted alkene.
Enantiospecific synthesis of a novel rearranged eunicellane diterpenoid by Sml2-Mediated cyclization
Schoettner, Elisabeth,Jones, Peter G.,Lindel, Thomas
experimental part, p. 3941 - 3956 (2010/03/26)
Aiming at the assembly of marine-derived diterpenoids, the synthesis and cyclization of a-geranylated carvones was investigated. 3-Hydroxyalkylation of side-chain hydrogenated carvone with geraniol-derived aldehydes gave access to diterpenoid allyl phosph
Studies directed toward the synthesis of the massileunicellins
Chai, Yonghai,McIntosh, Matthias C.
, p. 3269 - 3272 (2007/10/03)
An approach to the massileunicellins is described that employs a cycloaldol reaction to assemble the isobenzofuran bicyclic core. A stereoselective rearrangement-epoxidation-oxidation cascade and a chelation controlled addition to a hindered acyl furan are used to install the C3, C11, C12, and C13 oxygens. The synthesis establishes eight of the nine stereocenters present in the isobenzofuran core of the massileunicellins.
