154699-13-5Relevant academic research and scientific papers
Enantioselective formal total synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol - Eschenmoser/Claisen rearrangement
Yoshida, Masahiro,Shoji, Yasunobu,Shishido, Kozo
experimental part, p. 5053 - 5058 (2010/08/20)
The enantioselective formal total synthesis of aplysin has been achieved utilizing a palladium-catalyzed addition of arylboronic acid to the allenic alcohol followed by the Eschenmoser/Claisen rearrangement as the key steps.
A Remarkable Substituent Effect on the Enantioselectivity of Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols: A New Enantiocontrolled Synthesis of (-)-Debromoaplysin and (-)-Aplysin
Nemoto, Hideo,Nagamochi, Masatoshi,Ishibashi, Hiroki,Fukumoto, Keiichiro
, p. 74 - 79 (2007/10/02)
A remarkable substituent effect by the tert-butyldimethylsiloxy group on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2--2-cyclopropylideneethanol (18), affording (S)-(-)-2--2-hydroxymethylcyclobutanone (21) in high yield and high enantiomeric excess, was observed.This enabled us to accomplish a concise and highly enantioselective total synthesis of (-)-debromoaplysin (2) and (-)-aplysin (1), providing a new and general strategy for the enantioselective synthesis of biologically important substances having the dihydrobenzofuran framework.
