Two-directional synthesis of the non-adjacent bis(tetrahydrofuran) core of cis-sylvaticin

作者：Quinn Kevin J^*; Gage Kaylie E; Stanners Caroline M; Hayes Colin O; Shanley Kathleen E; Couvertier Shalise M

来源：Tetrahedron Letters, 2014, 55(2): 376-378.

DOI：10.1016/j.tetlet.2013.11.032

• Annonaceous acetogenins
• Silicon-tethered metathesis
• Dihydroxylation
• Two-directional synthesis

Synthesis of the C(2-)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/S(N)2 cyclization, is employed.

• 出版日期2014-1-8