A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

作者：Usui Kenji; Suzuki Takahiro; Nakada Masahisa^*

来源：Tetrahedron Letters, 2015, 56(10): 1247-1251.

DOI：10.1016/j.tetlet.2015.01.139

• Diels-Alder reaction
• Intramolecular
• Natural product
• Stereoselective
• Synthesis

A highly stereoselective intramolecular Diels Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.

• 出版日期2015-3-4