126570-34-1Relevant academic research and scientific papers
Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes
Serra, Stefano
experimental part, 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.
Intra- and intermolecular photocyclization of vinylbenzo-1,4-quinones
Iwamoto, Hidetoshi,Takuwa, Akio,Hamada, Kensaku,Fujiwara, Ryuji
, p. 575 - 581 (2007/10/03)
The photochemical reactions of a variety of vinylbenzo-1,4-quinones have been investigated. Irradiation of a benzene solution of 2-methyl-5-(1-phenylvinyl)benzo-1,4-quinone affords quantitatively a benzofuranol via intramolecular cyclization, while the st
Synthesis of Two Monoterpenic Hydroquinone Dimethyl Ethers Ocurring in Calea pilosa Baker
Sudalai, A.,Rao, G. S. Krishna
, p. 520 - 521 (2007/10/02)
Two monoterpenic hydroquinone dimethyl ethers (1) and (2) have been synthesized starting from a common intermediate, 2,5-dimethoxy-4-methylacetophenone (4).Reaction of N-bromosuccinimide on 4 gives the bromomethyl compound (5) which is converted into the keto acetate (6) by exchange with OAc-.Grignard reaction with CH3MgI transforms 6 to 8 from which 1 is obtained by oxidative dehydration with MnO2.Compound (2) is obtained from 4 by the action of CH3MgI followed by dehydration with MnO2.
