Schobert Rainer, Jagusch Carsten, Melanophy Claire, Mullen Gillian
Organic Chemistry Laboratory, University of Bayreuth, D-95440, Bayreuth, Germany.
Org Biomol Chem. 2004 Dec 7;2(23):3524-9. doi: 10.1039/b412779j. Epub 2004 Nov 5.
Polystyrene-bound cumulated ylide Ph3PCCO was prepared on a large scale in two steps. It reacts with Grignard compounds, amines and alcohols to give immobilized acyl, amide and ester ylides, respectively. Their Wittig reactions lead to alkenes free of phosphane oxide. Optically pure 5-substituted tetramates were obtained from reactions of resin-bound Ph3PCCO with alpha-ammonium esters in one step. The mycotoxin (-)-tenuazonic acid was accordingly prepared in just three steps.
聚苯乙烯负载的累积叶立德Ph3PCCO通过两步法大规模制备。它与格氏试剂、胺和醇反应，分别生成固定化的酰基、酰胺和酯叶立德。它们的维蒂希反应生成不含氧化膦的烯烃。光学纯的5-取代四酰胺可通过树脂负载的Ph3PCCO与α-铵酯一步反应得到。霉菌毒素（-）-细交链孢菌酮酸因此仅通过三步就得以制备。
