Total Synthesis of Panaginsene
Vipin Kumar Singh, Tushar Kanti Chakraborty
Abstract
The total synthesis of panaginsene has been accomplished in 11 linear steps starting from methyl 3,3-dimethyl-5-oxocyclopent-1-ene-1-carboxylate. The key steps are a Sharpless asymmetric epoxidation and Ti(III)-mediated reductive epoxide opening-radical cyclization to construct the chiral quaternary carbon stereocenter followed by a very challenging HWE olefination reaction on an 1,3-keto aldehyde and a late stage McMurry olefination using low valent titanium to construct the highly constrained angular tetrasubstituted olefin in a five-membered ring.
Topics & Concepts
StereocenterOlefin fiberQuaternary carbonAldehydeEpoxideChemistryRing (chemistry)StereochemistryTotal synthesisCarboxylateRadical cyclizationOrganic chemistryEnantioselective synthesisMedicinal chemistryCatalysisMarine Sponges and Natural ProductsOxidative Organic Chemistry ReactionsSynthetic Organic Chemistry Methods