The secondary metabolite, turkiyenine, is a probable bioactive component of the medicinal plant, Hypecoum procumbens L. Structurally, it is an isoquinoline-derived alkaloid composed of dihydrobenzofuran and 3-benzazepine-1-one moieties arranged in a unique spirocyclic structure. Yet despite the intriguing structure and medicinal relevance of benzofuran and benzazepine motifs, neither a synthetic study nor a biological evaluation of turkiyenine have been reported to date. Herein we communicate the first total synthesis of the proposed structure of turkiyenine, and on the basis of X-ray crystallography show that the proposed structure is incorrect. The key steps of our synthesis include an aza-spiro annulation onto a benzofuran using a rhodium–nitrenoid to construct a 3-alkyl-3-amino-2,3-dihydrobenzofuran, an acyl-alkylation of an aryne onto a β-ketolactam to form a 3-benzazepine-1-one, and chemoselective reduction of an amide in the presence of a ketone.

中文翻译：

---

Turkiyenine 拟议结构的全合成

次生代谢产物火鸡碱可能是药用植物 Hypecoum procumbens L 的生物活性成分。在结构上，它是一种异喹啉衍生的生物碱，由二氢苯并呋喃和 3-benzazepine-1-one 部分组成，以独特的螺环结构排列。然而，尽管苯并呋喃和苯并氮杂的基序具有有趣的结构和医学相关性，但迄今为止，尚未报道对土耳其宁的合成研究或生物学评估。在本文中，我们交流了所提出的 turkiyenine 结构的首次全合成，并且基于 X 射线晶体学表明所提出的结构是不正确的。我们合成的关键步骤包括使用铑-硝基化合物在苯并呋喃上进行氮杂-螺环化以构建 3-烷基-3-氨基-2,3-二氢苯并呋喃，