Synthesis and biological activity of [Tic(5)] didemnin B

Authors
Pfizenmayer, AJ Vera, MD Ding, XB Xiao, D Chen, WC Joullie, MM Tandon, D Toogood, PL
Citation
Aj. Pfizenmayer et al., Synthesis and biological activity of [Tic(5)] didemnin B, BIOORG MED, 8(24), 1998, pp. 3653-3656
Citations number
33
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
8
Issue
24
Year of publication
1998
Pages
3653 - 3656
Database
ISI
SICI code
0960-894X(199812)8:24<3653:SABAO[>2.0.ZU;2-3
Abstract
A didemnin B analog containing a Tic (1,2,3,3-tetrahydroisoquinoline-3-carb oxylic acid) as a conformationally restrained replacement for tyrosine has been synthesized and shown to have comparable potency as a protein biosynth esis inhibitor. Synthetic highlights include an oxidation of an alcohol to an acid in the presence of the sensitive Tic heterocycle and a modified Sch midt-type one-pot macrocyclization. (C) 1998 Elsevier Science Ltd. All righ ts reserved.