A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins
Authors:
- 22 June 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (15) , 5922-5931
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.Keywords
This publication has 65 references indexed in Scilit:
- Oxidative polycyclizations with rhenium(VII) oxidesPure and Applied Chemistry, 2002
- Rules of Stereoselectivity in Tandem Oxidative Polycyclization Reaction with Rhenium(VII) OxidesJournal of the American Chemical Society, 1998
- Highly Diastereoselective Cyclizations of Bishomoallylic Tertiary Alcohols Promoted by Rhenium(VII) Oxide. Critical Steric versus Chelation Effects in Alkoxyrhenium IntermediatesJournal of the American Chemical Society, 1998
- A Convergent Synthesis of (+)‐Parviflorin, (+)‐Squamocin K, and (+)‐5S‐HydroxyparviflorinAngewandte Chemie International Edition, 1997
- Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction1996
- Recent Advances in Asymmetric Wittig-Type Reactions.Acta Chemica Scandinavica, 1996
- An Efficient Bidirectional Approach to the C2-Symmetric Stereoisomers of the Bistetrahydrofuran Core of the AcetogeninsThe Journal of Organic Chemistry, 1996
- Acylperrhenate-Induced Tandem syn-Oxidative Cyclizations of HydroxydienesThe Journal of Organic Chemistry, 1995
- Combined Osmium-Rhenium Approach to Synthesis of Naturally Occurring PolyethersJournal of the American Chemical Society, 1995
- Molecular mode of action of annoninsPesticide Science, 1991