title: Total synthesis of (+)-monocerin via tandem dihydroxylation-S(N)2 cyclization and a copper mediated tandem cyanation-lactonization approach.
abstract: A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation-cyclization as the key steps.
authors.affiliation: CSIR-National Chemical Laboratory, Division of Organic Chemistry, Dr. Homi Bhabha Road, Pune, 411008, India. e.begari@ncl.res.in.
authors.forename: U
authors.initials: U
authors.lastname: Nookaraju
authors.forename: Eeshwaraiah
authors.initials: E
authors.lastname: Begari
authors.forename: Pradeep
authors.initials: P
authors.lastname: Kumar
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D003300:Copper / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D006900:Hydroxylation; D049934:Isocoumarins / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D061065:Polyketides / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003486:Cyanides; D049934:Isocoumarins; D007783:Lactones; D061065:Polyketides; D003300:Copper; C485193:monocerin