title: Total synthesis of (+)-spongistatin 1. An effective second-generation construction of an advanced EF Wittig salt, fragment union, and final elaboration.
abstract: A stereocontrolled, total synthesis of (+)-spongistatin 1 (1) has been achieved. Union of a second-generation EF Wittig salt (+)-3 with the advanced ABCD aldehyde (-)-4, followed by regioselective macrolactonization and global deprotection afforded (+)-spongistatin 1 (1). The longest linear sequence, 29 steps, proceeded in 0.5% overall yield.
authors.affiliation: Department of Chemistry, Monell Chemical Senses Center, 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: Wenyu
authors.initials: W
authors.lastname: Zhu
authors.forename: Shohei
authors.initials: S
authors.lastname: Shirakami
authors.forename: Chris
authors.initials: C
authors.lastname: Sfouggatakis
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Doughty
authors.forename: Clay S
authors.initials: CS
authors.lastname: Bennett
authors.forename: Yasuharu
authors.initials: Y
authors.lastname: Sakamoto
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D000447:Aldehydes; D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D007783:Lactones; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins