165879-51-6Relevant articles and documents
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.
Stereocontrolled route to some optically active β-hydroxy phosphine oxides using the stereoselective addition of metallated phosphine oxides to proline-derived keto aminals
O'Brien, Peter,Warren, Stuart
, p. 2117 - 2127 (2007/10/03)
An asymmetric Horner-Wittig addition reaction with a chiral auxiliary attached to the electrophile is described. The key step is the addition of metallated phosphine oxides to Mukaiyama's proline-derived keto aminals (for which improved syntheses are described) and a detailed study of the factors affecting the stereoselectivity of these reactions is presented. In particular, by suitable choice of metallation conditions, complementary stereoselectivities are observed: reactions in THF with no additives are syn selective (Felkin non-chelation control) whereas reactions in toluene with added lithium bromide are anti selective (Cram chelation control).
Stereocontrolled Synthesis of R or S Diphenylphosphinoyl Hydroxy Aldehydes and 1,2-Diols Using Bicyclic Aminals
O'Brien, Peter,Warren, Stuart
, p. 2681 - 2684 (2007/10/02)
Homochiral diphenylphosphinoyl hydroxy aldehydes 1 and 2 have been made by diastereoselective additions of metallated methyldiphenylphosphine oxides 10 to Mukaiyama's keto aminals 8 and 9.Reduction to diphenylphosphinoyl 1,2 diols 3 and 4 is also described.Sharpless asymmetric dihydroxylation provides an alternative route diphenylphosphinoyl 1,2 diols 3 and 4, the two approaches are compared.
