848645-02-3Relevant academic research and scientific papers
A divergent and stereoselective approach to phenolic 1,7-dihydroxy- bisabolane sesquiterpenes: Asymmetric total synthesis of (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid
Serra, Stefano,Cominetti, Alessandra A.
, p. 1110 - 1116 (2013/10/08)
The combined use of the Sharpless asymmetric epoxidation, a number of stereospecific chemical transformations, and the 3,5-hexadienoic acid benzannulation protocol allowed us to devise a new, divergent, and stereoselective approach to terpenes with a chir
First asymmetric total synthesis of (+)-curcutetraol
Zhang, Chenxia,Ito, Suguru,Hosoda, Naoya,Asami, Masatoshi
, p. 2552 - 2554 (2008/09/21)
The first asymmetric total synthesis of (+)-curcutetraol, a marine phenolic bisabolane-type sesquiterpene, was achieved in eight steps in ca. 50% overall yield. The chiral tertiary benzylic alcohol moiety in the o-position of a phenol was constructed in high optical yield (99% ee) by an asymmetric synthesis using a chiral aminal, (2R,5S)-2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane.
Asymmetric total synthesis of (+)-curcutetraol and (+)-sydonol
Ito, Suguru,Zhang, Chenxia,Hosoda, Naoya,Asami, Masatoshi
experimental part, p. 9879 - 9884 (2009/04/03)
The asymmetric total syntheses of (+)-curcutetraol and (+)-sydonol, phenolic bisabolane-type sesquiterpenoids having chiral tertiary alcohol moiety in the o-position of a phenol, were achieved in high enantiomeric excesses (99% ee). The chiral tertiary benzylic alcohol moiety of these compounds was constructed by an asymmetric synthesis using an easily available chiral aminal, (-)-(2R,5S)-2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane. The absolute configurations of both (+)-curcutetraol and?(+)-sydonol have been assumed to be S-configuration based on the stereochemical course of the well established asymmetric synthesis used in the syntheses.
