title: Synthesis of fully functionalized aglycone of lycoperdinoside A and B.
abstract: This article reported the synthesis of fully functionalized aglycone of lycoperdinoside A and B. Pd-catalyzed Stille-Migita cross coupling between E-vinyl iodide 6 and E-vinyl stannane 23 established the highly substituted E,E-diene unit present in lycoperdinoside A and B. The other two Z-olefins present in the molecule were introduced by means of cis-selective Horner-Wadsworth-Emmons reaction with Still-Gennari phosphonate. Evans syn- and anti-aldol reactions were utilized to fix six of the seven stereo centres present in the aglycone.
authors.affiliation: Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India. subhash@iict.res.in.
authors.forename: Balla
authors.initials: B
authors.lastname: Chandrasekhar
authors.forename: Sudhakar
authors.initials: S
authors.lastname: Athe
authors.forename: P Purushotham
authors.initials: PP
authors.lastname: Reddy
authors.forename: Subhash
authors.initials: S
authors.lastname: Ghosh
mesh_terms: D000478:Alkylation; D060326:Chemistry Techniques, Synthetic; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009844:Oligosaccharides; D011753:Pyrones