CAS: 1438-57-9; Grindelic Acid

上下游产品

Methyl Grindelate 1438-58-0

📜Methyl Grindelate置于氢氧化钾体系中,用 甲醇,水 用作溶剂,化学反应 48.0H,反应生成(2R,5S)-4,4'Aalpha,5,5',6',7',8',8'A-八氢-2',5,5',5',8'Abeta-五甲基螺[呋喃-2(3H),1'(4'H)-萘]-5-乙酸
参考文献:Stereocontrolled Synthesis Of Ent-Grindelic Acid. A Useful Example Of Diastereofacial Guidance In An Oxonium Ion-Initiated Pinacolic Ring Expansion
标题:Stereocontrolled Synthesis Of Ent-Grindelic Acid. A Useful Example Of Diastereofacial Guidance In An Oxonium Ion-Initiated Pinacolic Ring Expansion
摘要:An Enantioselective Synthesis Of (+)-Grindelic Acid Is Described,Confirming That The Dextrorotatory Enantiomer Is Antipodal To The Natural Diterpenoid. The Optically Pure Bicyclic Ketone 5 Representing The Ab Ring System Is Constructed From The Levorotatory Wieland-Miescher Ketone And Must Therefore Possess The Absolute Configuration Shown. Coupling Of 5 With The 5-Lithio Derivative Of Optically Active 2,3-Dihydrofuran 3 Derived From (R)-(-)-Linalool Was Effected For The Purpose Of Realizing Acid-Catalyzed Rearrangement With Generation Of The Appropriate Spirocyclic Framework. This Key Step Is Highly Stereocontrolled,Leading Predominantly To 7. Once The Advanced Intermediate 15 Is Available In This Fashion,Its Subsequent Exposure To Oxidation And Dehydration Steps Led To The Target Molecule. The Synthesis Demonstrates Unequivocally That Natural (-)-Grindelic Acid Is A True Labdane Diterpenoid.
Doi:10.1021/jo960547P