区域选择性螺甾烷 E 环开裂用于合成二氢吡喃甾体骨架。
Regioselective Spirostan E-Ring Opening for the Synthesis of Dihydropyran Steroidal Frameworks.
机构信息
Departamento de Física Aplicada, Centro de Investigación y de Estudios Avanzados , Unidad Mérida, Km 6 Antigua Carretera a Progreso, Apdo, Postal 73, Cordemex, Mérida, Yucatán 97310, México.
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos , Av Universidad 1001, Cuernavaca, Morelos C. P. 62209, México.
出版信息
Org Lett. 2016 Apr 15;18(8):1772-5. doi: 10.1021/acs.orglett.6b00492. Epub 2016 Mar 24.
The regioselective opening of the ring E in spirostan sapogenins provides new dihydropyran derivatives. This novel side chain is obtained after a Lewis acid mediated acetolysis followed by an alkaline workup. The reaction mechanism is analyzed via density functional theory computations, and both experimental and computational data support the formation of an oxacarbenium intermediate. The behavior of the title skeletons under acidic conditions is also investigated.
螺甾烷型皂甙元中环 E 的区域选择性开环提供了新的二氢吡喃衍生物。该新的侧链是在路易斯酸介导的乙酰解反应后，通过碱性处理得到的。通过密度泛函理论计算分析了反应机理，实验和计算数据均支持氧杂碳正离子中间体的形成。还研究了标题骨架在酸性条件下的行为。
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