528606-13-5Relevant academic research and scientific papers
Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes
Serra, Stefano
, p. 619 - 628 (2011/07/08)
A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished.
Enantioselective syntheses of the assigned structures of the helibisabonols A and B
Miyawaki, Akari,Osaka, Mayu,Kanematsu, Makoto,Yoshida, Masahiro,Shishido, Kozo
experimental part, p. 6753 - 6761 (2011/09/20)
The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the σ-symmetrical diol (route a) and a diastereoselective conjugate addition of the m
Enantioselective syntheses of heliannuols G and H
Morimoto, Sachie,Shindo, Mitsuru,Shishido, Kozo
, p. 69 - 73 (2007/10/03)
Enantioselective total syntheses of the proposed structures for heliannuols G and H have been accomplished. However, their spectral properties were not identical with those of the natural products.
Enantioselective total synthesis of (-)-heliannuol A
Kishuku, Hidetoshi,Shindo, Mitsuru,Shishido, Kozo
, p. 350 - 351 (2007/10/03)
An efficient and enantiocontrolled total synthesis of (-)-heliannuol A has been accomplished by employing ring closing metathesis and sequential diastereoselective epoxidation and regioselective reductive cleavage of the epoxide ring.
Enantioselective total synthesis of heliannuols D and A
Takabatake, Kenya,Nishi, Izumi,Shindo, Mitsuru,Shishido, Kozo
, p. 1807 - 1808 (2007/10/03)
The enantioselective total synthesis of heliannuols D and A, which exhibits allelopathic activity, was discussed. The enantioselective total synthesis included base-mediated intramolecular cyclisation of phenolic epoxide. The analysis showed the preparation of configurationally defined enantiopure epoxide whose intramolecular aryl ether-forming reaction provided heliannuol D and/or heliannuol A.
