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Total Synthesis of Cryptophycin 3
Author(s) -
Danner Paulami,
Bauer Matthias,
Phukan Prodeep,
Maier Martin E.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400558
Subject(s) - chemistry , depsipeptide , tripeptide , enantioselective synthesis , alkylation , stereochemistry , total synthesis , ring (chemistry) , amino acid , organic chemistry , catalysis , biochemistry
The depsipeptide cryptophycin 3 ( 5 ) and the cryptophycin analogue 43 were prepared from the corresponding four subunits. The tripeptide analogue 34 was acquired from the starting amino ester 33 , which contains fragments D and C. After extension at the carboxyl function by esterification with the hydroxy ester 10 , the seco compounds 37 and 42 were obtained. Ring closure was achieved by macrolactamization in the presence of TBTU as condensing agent. This work features a streamlined synthesis of the hydroxy ester 10 , a short synthesis of the amino acid 14 by enantioselective alkylation of the glycinimine 21 , and the use of the Fmoc protecting group for the amino functions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)