title: Total synthesis and stereochemical revision of acortatarins A and B.
abstract: A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole and spiroketalization.
authors.affiliation: Organic Chemistry Division-II, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 607, India. gsudhakar@iict.res.in
authors.forename: Gangarajula
authors.initials: G
authors.lastname: Sudhakar
authors.forename: Vilas D
authors.initials: VD
authors.lastname: Kadam
authors.forename: Shruthi
authors.initials: S
authors.lastname: Bayya
authors.forename: Gavinolla
authors.initials: G
authors.lastname: Pranitha
authors.forename: Bharatam
authors.initials: B
authors.lastname: Jagadeesh
mesh_terms: D029023:Acorus / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004852:Epoxy Compounds; D009025:Morpholines; D013141:Spiro Compounds; C550646:acortatarin A; C550647:acortatarin B