呋喃甾族化合物研究。渥曼青霉素A、B、E环核心的立体选择性合成。
Furanosteroid studies. Stereoselective synthesis of the A,B,E-ring core of wortmannin.
作者信息
Sessions E Hampton, O'Connor Roger T, Jacobi Peter A
机构信息
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
出版信息
Org Lett. 2007 Aug 16;9(17):3221-4. doi: 10.1021/ol071158s. Epub 2007 Jul 26.
Alkyne oxazole 11c is converted in three steps, and approximately 45% overall yield, to furanolactone 21alpha having the A,B,E-ring core of the wortmannin (2) family of furanosteroids. The TiCl4-catalyzed insertion of EtO2C-CH=O between C3 and C10 in furanoacid 14d is >98% stereoselective via a pathway involving chemoselective lactonization of equilibrating aldol intermediates 23alpha,beta (dynamic kinetic resolution).
炔基恶唑11c经三步反应转化为呋喃内酯21α，总收率约为45%，该呋喃内酯具有渥曼青霉素（2）家族呋喃甾类化合物的A、B、E环核心结构。在四氯化钛催化下，呋喃酸14d中C3和C10之间插入乙氧羰基甲醛，通过涉及平衡醛醇中间体23α,β的化学选择性内酯化途径（动态动力学拆分），立体选择性大于98%。
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