8-O-Acetyl-8-epi-9-deoxygoniopypyrone
نویسندگان
چکیده
THE TITLE COMPOUND (SYSTEMATIC NAME 7-oxo-3-phenyl-2,6-dioxabicyclo-[3.3.1]nonan-4-yl acetate), C(15)H(16)O(5), is a styryllactone derivative which was isolated from Goniothalamus macrophyllus. The mol-ecule has two fused rings consisting of a tetra-hydro-2H-pyran and a lactone ring, with the benzene ring and the acetyl group attached to the tetra-hydro-2H-pyran ring. The tetra-hydro-2H-pyran ring is in a standard chair conformation, whereas the lactone ring is in an envelope conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into sheets parallel to the ac plane. Weak C-H⋯π inter-actions are also observed.
منابع مشابه
Approaches to the synthesis of 8-epi-vernolepin from germacrolides
As part of our program aimed at the synthesis of bioactive products, the enantiospecific synthesis of 8-epi-vernolepin derivatives, starting from accessible germacrolides, was attempted. Synthesis of (1)-8-O-acetyl-1,2,11β,13-tetrahydro-8-epi-vernolepin (23) from (1)-salonitenolide (6) was performed in nine steps with an acceptable overall yield. On the other hand, the synthesis from (1)-stenop...
متن کاملAsymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition.
The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine (20% yield over...
متن کاملThe release and purification of sialic acids from glycoconjugates: methods to minimize the loss and migration of O-acetyl groups.
The sialic acids can have O-acetyl esters at the 4, 7, 8, and 9 positions. Most methods for the detailed study of such molecules require their release from glycosidic linkage, followed by extensive purification. The currently used methods for release and purification of sialic acids allow a reasonable qualitative analysis of the diversity of sialic acids from a given biological source. However,...
متن کاملNew chemical constituents of roots of Urtica triangularis HAND-MASS.
Studies on the chemical constituents of roots of Urtica triangularis HAND-MASS have led to the isolation of four new compounds. The structures, including the absolute configurations, of these constituents have been elucidated through spectral studies including (1)H-NMR, (13)C-NMR, 2D-NMR experiments (heteronuclear single-quantum coherence, heteronuclear multiple bonding connectivity and nuclear...
متن کاملEnantioselective Total Synthesis of the Reported Structures of (−)-9-epi-Presilphiperfolan-1-ol and (−)-Presilphiperfolan-1-ol: Structural Confirmation and Reassignment, New Biosynthetic Insights
Presilphiperfolanols (also known as prebotrydials) are members of a family of natural products that are important biosynthetic precursors to diverse sesquiterpenoids (Figure 1).[i, ii, iii, iv] To date, four members of the group have been isolated: presilphiperfolan-1-ol (1),[v] 9-epi-presilphiperfolan-1-o l (2),[vi] presilphiperfolan-8-ol (3),[ii] and presilphiperfolan-9-ol (4),[vii] with 1 an...
متن کامل