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Syntheses of novel 4-tert-alkyl ether proline-based 16- and 17-membered macrocyclic compounds
Kevin X Chen1, F George Njoroge, Bancha Vibulbhan
1Schering-Plough Research Institute, 2015 Galloping Hill Road, K-15-3-3545, Kenilworth, NJ 07033, USA. Kevin.chen@spcorp.com
The Journal of Organic Chemistry
|April 13, 2002
Abstract:
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.