title: Radical Approach to the Chiral Quaternary Center in Asperaculin A: Synthesis of 9-Deoxyasperaculin A.
abstract: Diastereoselective approaches toward the synthesis of a marine-derived sesquiterpenoid fungal metabolite, asperaculin A, are delineated, combining step economy and simplicity. Two distinct lactonization sequences from a common intermediate led to the first synthesis of 9-deoxyasperaculin A, a novel dioxa[5.5.5.6]fenestrane, in 14 steps (16% overall yield) and 16 steps (18% overall yield), respectively. [2,3]-Wittig-Still rearrangement and Ti(III)-mediated epoxide opening-cyclization were employed as some of the key steps for the stereoselective generation of the vicinal all-carbon quaternary centers of the target molecule.
authors.affiliation: CSIR-Central Drug Research Institute , Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.
authors.forename: Dipendu
authors.initials: D
authors.lastname: Das
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore 560012, India.
authors.forename: Tushar Kanti
authors.identifier: 0000-0003-4301-3672
authors.initials: TK
authors.lastname: Chakraborty