Macrocyclic peptide inhibitors of serine proteases. Convergent total synthesis of cyclotheonamides A and B via a late-stage primary amine intermediate. Study of …

…, P Andrade-Gordon, JA Kauffman…

Index: Maryanoff, Bruce E.; Greco, Michael N.; Zhang, Han-Cheng; Andrade-Gordon, Patricia; Kauffman, Jack A.; Nicolaou; Liu, Aijun; Brungs, Peter H. Journal of the American Chemical Society, 1995 , vol. 117, # 4 p. 1225 - 1239

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Citation Number: 91

Abstract

Abstract: Cyclotheonamide A (CtA, 1), a cyclic pentapeptide isolated from the marine sponge Theonella sp., is an inhibitor of serine proteases such as a-thrombin and trypsin. We describe, in detail, our total synthesis of CtA by a convergent [3+ 21 fragment-condensation route. The requisite protected amino acid starting materials were processed and converted into two segments, A (13) and B (21), which were coupled with BOP reagent in 75% yield ( ...