新型基于4-叔丁基醚脯氨酸的16元和17元大环化合物的合成。
Syntheses of novel 4-tert-alkyl ether proline-based 16- and 17-membered macrocyclic compounds.
作者信息
Chen Kevin X, Njoroge F George, Vibulbhan Bancha, Buevich Alexei, Chan Tze-Ming, Girijavallabhan Viyyoor
机构信息
Schering-Plough Research Institute, 2015 Galloping Hill Road, K-15-3-3545, Kenilworth, NJ 07033, USA.
出版信息
J Org Chem. 2002 Apr 19;67(8):2730-3. doi: 10.1021/jo020075g.
Starting from N-Cbz-4-hydroxyproline methyl ester 1, a boron trifluoride-diethyl etherate-catalyzed reaction provided 4-tert-alkyl ether proline 4. Two deprotections and amide bond formations furnished the phenol alcohol 2. The macrocyclization of 2 was accomplished through a Mitsunobu reaction using triphenylphosphine and 1,1'-(azodicarbonyl)dipiperidine (ADDP), to afford novel 16- and 17-membered proline-based macrocyclic compounds of type 3.
从N-Cbz-4-羟基脯氨酸甲酯1开始，在三氟化硼-二乙醚催化下反应得到4-叔烷基醚脯氨酸4。经过两步脱保护和酰胺键形成反应得到酚醇2。化合物2通过使用三苯基膦和1,1'-（偶氮二甲酰）二哌啶（ADDP）的 Mitsunobu 反应进行大环化，得到新型的16元和17元脯氨酸基大环化合物3。
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