An Enantioselective Biomimetic Total Synthesis of (−)‐Siccanin

作者：Barry M. Trost, Hong C. Shen, Jean‐Philippe Surivet · 发表于：Angewandte Chemie International Edition · 年份：2003 · DOI：10.1002/anie.200351868 · 被引用次数：101 · 研究领域：Chemical synthesis and alkaloids、Alkaloids: synthesis and pharmacology、Traditional and Medicinal Uses of Annonaceae

A convergent asymmetric synthesis of the clinically important antifungal agent (−)-siccanin (1) mimics the proposed biosynthetic pathway. A Pd-catalyzed asymmetric allylic alkylation was used to establish the stereochemistry, and sequential radical processes (a TiIII-promoted cyclization followed by diacetoxyiodobenzene-promoted tetrahydrofuran formation) led to the completion of the first asymmetric synthesis of 1.