Tetrahedron

(±)-Diinsininone: made nature's way

C Selenski, TRR Pettus

文献索引：Selenski, Carolyn; Pettus, Thomas R.R. Tetrahedron, 2006 , vol. 62, # 22 p. 5298 - 5307

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被引用次数: 63

摘要

We report the synthesis of diinsininone (33), the aglycone of (±)-diinsinin (2). Thereby, we complete the first construction of a proanthocyanidin (PA) type-A compound incorporating a [3.3. 1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) ...