Title of article
Two-directional synthesis of the non-adjacent bis(tetrahydrofuran) core of cis-sylvaticin
Author/Authors
Quinn، نويسنده , , Kevin J. and Gage، نويسنده , , Kaylie E. and Stanners، نويسنده , , Caroline M. and Hayes، نويسنده , , Colin O. and Shanley، نويسنده , , Kathleen E. and Couvertier، نويسنده , , Shalise M.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2014
Pages
3
From page
376
To page
378
Abstract
Synthesis of the C2-symmetric, non-adjacent bis(tetrahydrofuran) core of cis-sylvaticin in seven steps and 24% overall yield from (2R,3S)-1,2-epoxy-4-penten-3-ol is reported. A strategy involving assembly of the central 1,4-diol unit by silicon-tethered ring-closing metathesis and subsequent two-directional functionalization, including establishment of the cis/threo stereochemical relationships of the tetrahydrofuran rings by Sharpless asymmetric dihydroxylation/SN2 cyclization, is employed.
Keywords
Annonaceous acetogenins , Silicon-tethered metathesis , Two-directional synthesis , dihydroxylation
Journal title
Tetrahedron Letters
Serial Year
2014
Journal title
Tetrahedron Letters
Record number
1887538
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