A strategy toward the synthesis of C-13-oxidized cembrenolides

作者：Saitman Alec; Sullivan Steven D E; Theodorakis Emmanuel A^*

来源：Tetrahedron Letters, 2013, 54(12): 1612-1615.

DOI：10.1016/j.tetlet.2013.01.085

• Cembrane
• Macrocyclization
• Furan oxidation
• Anomeric effect
• Hemiketal

An efficient strategy for the construction of C-13-oxidized cembrenolides is reported. Central to this strategy is the installation of the C-13 hydroxyl group prior to cembrane macrocyclization (via formation of the C-1-C-2 bond), allowing access to both C-13 alcohol epimers. The orientation of the C-13 alcohol was found to influence the cyclization mode of the cembranolide scaffold upon furan oxidation, leading to motifs reminiscent to bipinnatolide F, bielschowskysin, and verrillin.

• 出版日期2013-3-20