Synthesis of Optically Active Cyclopenta[c]pyran-4-carboxylic Acid Derivatives, Building Blocks for Iridoids. An Attractive Alternative to Asymmetric de Mayo Reaction
- 1 November 1989
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 18 (11) , 1925-1928
- https://doi.org/10.1246/cl.1989.1925
Abstract
A new asymmetric de Mayo reaction leading to enantiomerically pure iridoids has been elaborated using chiral spirocyclic dioxinone as the photochemical equivalent of diformylacetate.Keywords
This publication has 15 references indexed in Scilit:
- A double Diels-Alder reaction of a C2-symmetric bis-dienophile: A new enantioselective approach to natural loganinTetrahedron Letters, 1987
- Photocycloaddition, methylation, and catalytic reduction of chiral spirocyclic 1,3-dioxin-4-ones: Different stereofacial selectivity and its explanation.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- Iridoids : enantioselective synthesis of loganin via an asymmetric diels-alder reactionTetrahedron, 1986
- Iridoids : The structure elucidation of specionin based on chemical evidence and 1H NMR analysisTetrahedron, 1986
- Stereocontrolled Synthesis of (+)‐Sarracenin via Photochemical CycloadditionAngewandte Chemie International Edition in English, 1982
- An Efficient Stereoselective Synthesis of (±)‐Sweroside and (±)‐secologanin aglucone O‐methyl ethers. Preliminary communicationHelvetica Chimica Acta, 1978
- Asymmetric synthesis of loganin. Stereospecific formation of (1R,2R)- and (1S,2S)-2-methyl-3-cyclopenten-1-ol and (2R)- and (2S)-2-methylcyclopentanoneJournal of the American Chemical Society, 1973
- Total synthesis of loganinJournal of the American Chemical Society, 1973
- Photochemical syntheses. 37. Enone photoannelationAccounts of Chemical Research, 1971
- Total synthesis of loganinJournal of the American Chemical Society, 1970