title: Spongistatin synthetic studies. evolution of a scalable synthesis for the EF fragment of (+)-Spongistatin 1 exploiting a Petasis-Ferrier union/rearrangement tactic.
abstract: [structure: see text] An efficient, stereocontrolled, and scalable second-generation synthesis of (+)-3, an advanced EF subtarget for the total synthesis of (+)-spongistatin 1, has been achieved. Highlights of the strategy include preparation of the F-ring pyran via a Petasis-Ferrier union/rearrangement sequence and installation of the chlorodiene side chain employing a cyanohydrin alkylation. The longest linear sequence, 26 steps, proceeds in 8.3% overall yield.
authors.affiliation: Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: Chris
authors.initials: C
authors.lastname: Sfouggatakis
authors.forename: Dimitar B
authors.initials: DB
authors.lastname: Gotchev
authors.forename: Shohei
authors.initials: S
authors.lastname: Shirakami
authors.forename: David
authors.initials: D
authors.lastname: Bauer
authors.forename: Wenyu
authors.initials: W
authors.lastname: Zhu
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Doughty
mesh_terms: D000818:Animals; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D018942:Macrolides / Q000032:analysis / Q000138:chemical synthesis*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D007202:Indicators and Reagents; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins