title: Total Synthesis and Configurational Assignment of Ascospiroketal A.
abstract: The total synthesis of the marine fungus-derived natural product ascospiroketal is described. This concise synthesis relies on a unique Ag(I) -promoted tandem cascade cyclization that provides direct access to the correctly configured tricyclic core of the natural product from a linear precursor. The synthesis of candidate stereostructures of ascospiroketal A allowed for the confident assignment of both the relative and absolute stereochemistry of this unusual octaketide.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6 (Canada).
authors.forename: Stanley
authors.initials: S
authors.lastname: Chang
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6 (Canada).
authors.forename: Soo
authors.initials: S
authors.lastname: Hur
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6 (Canada). rbritton@sfu.ca.
authors.forename: Robert
authors.initials: R
authors.lastname: Britton
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008386:Marine Biology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004988:Ethers, Cyclic; D013141:Spiro Compounds; C518010:ascospiroketal A
keywords: ascospiroketal A; chlorohydrins; natural products; spiroacetals; total synthesis