Stereoselective and Regiodivergent Allylic Suzuki鈥揗iyaura Cross-Coupling of 2-Ethoxydihydropyranyl Boronates: Synthesis and Confirmation of Absolute Stereochemistry of Diospongin B
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- 作者：Taras Rybak ; Dennis G. Hall
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：September 4, 2015
- 年：2015
- 卷：17
- 期：17
- 页码：4156-4159
- 全文大小：350K
- ISSN：1523-7052
文摘
Oxygen-containing heterocycles such as pyrans are a common substructure present in a variety of natural products and pharmaceutical drugs. Highly functionalized 4- and 6-aryl/heteroaryl dihydropyran derivatives are assembled by a highly stereoselective, ligand-controlled regiodivergent sp3鈥搒p2 Suzuki鈥揗iyaura cross-coupling of a 2-ethoxy dihydropyranyl boronate derived from a catalytic enantioselective inverse-electron-demand oxa[4 + 2] cycloaddition. The scope and selectivity of this method were assessed along with an application to a concise total synthesis of the diarylheptanoid natural product diospongin B.