Synthesis of natural product inulavosin via Ga(OTf)3-Catalyzed Hetero Diels–Alder Dimerization of salicyl alcohol derivative
Inulavosin, a natural melanogenesis inhibitor, has been synthesized smoothly from readily available and inexpensive starting materials by using a Ga(OTf)3-catalyzed room temperature hetero Diels–Alder dimerization of salicyl alcohol derivative and a regioselective phenol monobromination as the key steps.
The title compound, C23H28O2, was obtained from the reaction of acetone with meta-cresol. The molecular structure consists of two identical subunits which are nearly perpendicular to each other. The oxygen-containing rings are not planar and the molecule is chiral. The crystal structure consists of chains of molecules of the same chirality arranged along the [010] axis.
Ejsmont, Krzysztof,Kyziol, Janusz,Nowakowska, Ewa,Zaleski, Jacek
p. 93 - 94
(2007/10/03)
Synthesis of flavans: One-pot synthesis of flavans from 4- methylcoumarins
4-Methylcoumarins (2), obtained by condensation of suitable phenols (1) with ethyl acetoacetate in the presence of sulfuric acid, lead directly to flavans (3) when refluxed with sodium hydroxide and ethanediol.
Kamat, Vijayendra P.,Asolkar, Ratnakar N.,Kirtany, Janardan K.
p. 4581 - 4587
(2007/10/03)
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