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Synthesis of [S‐[1‐ 14 C]Val 7 ]VALSPODAR application of (+)/(−)‐[ 13,14 C n ]BABS and (+)/(−)‐[ 13,14 C n ]DPMGBS , part 4
Author(s) -
Burtscher P.,
Kohler B.,
Metz Y.,
Voges R.,
Wenger R.
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(20000315)43:3<205::aid-jlcr303>3.0.co;2-4
Subject(s) - chemistry , synthon , yield (engineering) , iodide , alkylation , carbon chain , stereochemistry , isopropyl , methyl iodide , medicinal chemistry , organic chemistry , materials science , metallurgy , catalysis
VALSPODAR 2 , a cyclic undecapeptide anticancer drug derived from natural Cyclosporin D 10 , was labelled with Carbon‐14 in a nine step synthesis. The sequence started from (−)‐[1‐ 14 C]BABS 1a , a highly versatile two‐carbon synthon for a broad spectrum of singly/multiply labelled substance classes, which after conversion to (−)‐[1‐ 14 C]DPMGBS 1b and subsequent alkylation with isopropyl iodide gave e.p. N‐Boc‐S[1‐ 14 C]valine 7 in 46% yield. Coupling to the respective linear decapeptide P 8→6 D , followed by cyclization and selective oxidation afforded the labelled drug substance in an overall radiochemical yield of 9%. Copyright © 2000 John Wiley & Sons, Ltd.