cas 158440-71-2, Irofulven | Articles data

Articles about 158440-71-2Total 5 be found

Total synthesis of hydroxymethylacylfulvene, an antitumour derivative of illudin S
(±)-Hydroxymethylacylfulvene is synthesized in 14 steps from 4-hydroxy-5-methyl-2-cyclopenten-1-one and 1-acetyl-1-(diazoacetyl)cyclopropane in 15% overall yield.
McMorris, Trevor C.,Hu, Yi,Yu, Jian,Kelner, Michael J.
p. 315 - 316
(1997)
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ILLUDIN ANALOGS, USES THEREOF, AND METHODS FOR SYNTHESIZING THE SAME
This invention provides illudin derivatives, intermediates, preparation methods, pharmaceutical compositions and uses thereof. Specific examples include novel synthetic routes to prepare illudin derivatives and an illudin derivative having a positive optical rotation, which has therapeutic value.
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(2020/03/29)

Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven
(Chemical Equation Presented) We report our full account of the enantioselective total synthesis of (-)-acylfulvene (1) and (-)-irofulven (2), which features metathesis reactions for the rapid assembly of the molecular framework of these antitumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketenethioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent IPNBSH for a late-stage reductive allylic transposition reaction, and (4) the final RCM/dehydrogenation sequence for the formation of (-)-acylfulvene (1) and (-)-irofulven (2).
Siegel, Dustin S.,Piizzi, Grazia,Piersanti, Giovanni,Movassaghi, Mohammad
scheme or table
p. 9292 - 9304
(2010/03/04)

Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven
(Chemical Equation Presented) Antitumor agents (-)-acylfulvene and (-)-irofulven are prepared in an approach that employs the powerful enyne ring-closing metathesis reaction to secure the spiro-bicyclic AB rings. Other key features of this synthesis include an efficient aldol-based introduction of the stereocenter at C2, a diazene-mediated reductive allylic transposition, and a ring-closing metathesis/oxidation sequence.
Movassaghi, Mohammad,Piizzi, Grazia,Siegel, Dustin S.,Piersanti, Giovanni
p. 5859 - 5863
(2007/10/03)

Synthesis of [3H]-illudin S, [3H]-acylfulvene, [3H]and[14C]- hydroxymethylacylfulvene (MGI 114)
Tritiated derivatives of the toxic sesquiterpene illudin S (1) have been prepared by fermentation of Omphalotus illudens in the presence of [3H]- sodium acetate. [3H]-illudin S was converted to antitumor [3H]-acylfulvene (4) by treatment with dilute sulfuric acid. Antitumor [14C]- hydroxymethylacylfulvene (5) was best prepared by reacting acylfulvene with [14C]-paraformaldehyde in dilute sulfuric acid.
McMorris, Trevor C.,Yu, Jian,Herman, David M.,Kelner, Michael J.,Dawe, Robin,Minamida, Akira
p. 279 - 285
(2007/10/03)