新型螺环苯并呋喃酮-六氢山酮素-吡啶类化合物的非对映选择性合成

Diastereoselective Synthesis of Novel Spirobenzofuran-hexahydroxanthone-pyridine Hybrids

以苯并呋喃酮-色酮合成子与吡啶查尔酮为原料,在DBU催化下,在二氯甲烷中发生Michael/Michael加成关环反应,非对映选择性合成了11个未见文献报道的螺环苯并呋喃酮-六氢山酮素-吡啶类化合物(3a~3k),产率为46%~65%,dr值为6/1~11/1,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,并进一步通过单晶确定化合物3g的相对构型。结果表明:该类化合物含有连续5个立体中心,以及一个具有潜在生物活性的六氢山酮素骨架和苯并呋喃酮骨架,可以为生物活性筛选提供物质基础。

Eleven novel spirobenzofuran-hexahydroxanthone-pyridine hybrids(3a~3k)were diastereoselectively synthesized via a DBU-catalyzed Michael/Michael cycloaddition of benzofuranone-chromone synthons with pyridinchalones 2 under room temperature conditions in CH_(2)Cl_(2) for 12 h.The yields and dr of 3a~3k were 46%~65%and 6/1~11/1,respectively.The structures of products were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The configuration of compound 3g was further determined by the single crystal.These compounds bear five contiguous stereogenic centers,including a potential bioactive hexahydroxanthin skeleton and benzofuranone skeleton,which can provide a material basis for bioactivity screening.