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Synthesis of [ 3 H]‐illudin S, [ 3 H]‐acylfulvene, [ 3 H] & [ 14 C]‐hydroxymethylacylfulvene (MGI 114)
Author(s) -
McMorris Trevor C.,
Yu Jian,
Herman David M.,
Kelner Michael J.,
Dawe Robin,
Minamida Akira
Publication year - 1998
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(199804)41:4<279::aid-jlcr86>3.0.co;2-j
Subject(s) - chemistry , paraformaldehyde , sulfuric acid , sesquiterpene , fermentation , organic chemistry , stereochemistry
Tritiated derivatives of the toxic sesquiterpene illudin S ( 1 ) have been prepared by fermentation of Omphalotus illudens in the presence of [ 3 H]‐sodium acetate. [ 3 H]‐illudin S was converted to antitumour [ 3 H]‐acylfulvene ( 4 ) by treatment with dilute sulfuric acid. Antitumor [ 14 C]‐hydroxymethylacylfulvene ( 5 ) was best prepared by reacting acylfulvene with [ 14 C]‐paraformaldehyde in dilute sulfuric acid. © 1998 John Wiley & Sons, Ltd.