title: A bidirectional approach to the synthesis of a complete library of adjacent-bis-THF annonaceous acetogenins.
abstract: Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.
authors: The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors: Sanjib
authors: S
authors: Das
authors: Lian-Sheng
authors: LS
authors: Li
authors: Sunny
authors: S
authors: Abraham
authors: Zhiyong
authors: Z
authors: Chen
authors: Subhash C
authors: SC
authors: Sinha
mesh_terms: D054378:Acetogenins; D029061:Annonaceae / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology; D002412:Cations; D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D010084:Oxidation-Reduction; D012211:Rhenium / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D054378:Acetogenins; D000972:Antineoplastic Agents, Phytogenic; D002412:Cations; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; D012211:Rhenium