Title of article :
Chiral base route to cyclic polyols: asymmetric synthesis of aminodeoxyconduritols and conduritol F
Author/Authors :
de Sousa، نويسنده , , Simon E and OʹBrien، نويسنده , , Peter and Pilgram، نويسنده , , Christopher D، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2001
Abstract :
A chiral base route from a meso cyclohexene oxide to an allylic alcohol provides key intermediates for the synthesis of cyclic polyols. A Mitsunobu approach and an Overman rearrangement approach transform allylic alcohols into some aminodeoxyconduritols (95% ee). Elaboration of a chiral enone (89% ee) via (i) α-hydroxylation and (ii) stereoselective reduction completes a high yielding synthesis of the tetraacetate of conduritol F.
Keywords :
Allylic alcohols , Cyclitols , epoxides , Rearrangement
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters