Title of article
Total synthesis of (−)-centrolobine: β-C-glycoside formation via a tandem Grignard addition and stereoselective hemi-ketal reduction
Author/Authors
Jennings، نويسنده , , Michael P. and Clemens، نويسنده , , Ryan T.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2005
Pages
4
From page
2021
To page
2024
Abstract
It has been demonstrated that an aryl-β-C-glycoside can be efficiently constructed via a sequence consisting of Brown asymmetric allylation, ring-closing metathesis, hydrogenation, nucleophilic addition, and stereoselective Et3SiH reduction. The antibiotic natural product (−)-centrolobine was synthesized in this manner utilizing only five steps with an overall 53% yield.
Keywords
tetrahydropyran , C-glycoside , Centrolobine , ring-closing metathesis , one-pot reaction
Journal title
Tetrahedron Letters
Serial Year
2005
Journal title
Tetrahedron Letters
Record number
1845134
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