title: Spongistatin synthetic studies. An efficient, second-generation construction of an advanced ABCD intermediate.
abstract: [reaction: see text] A short, efficient, and stereocontrolled synthesis of (-)-4, an advanced ABCD subunit of the spongistatins, has been achieved. Central to the synthetic strategy is the multicomponent linchpin union of silyl dithianes with epoxides to access both the AB and CD fragments. Fragment coupling was then achieved via an efficient stereoselective aldol reaction. The linear sequence required 22 steps and proceeded in 4.0% overall yield.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Doughty
authors.forename: Chris
authors.initials: C
authors.lastname: Sfouggatakis
authors.forename: Clay S
authors.initials: CS
authors.lastname: Bennett
authors.forename: Jyunichi
authors.initials: J
authors.lastname: Koyanagi
authors.forename: Makoto
authors.initials: M
authors.lastname: Takeuchi
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D007783:Lactones; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins