158440-71-2

Basic information

• Product Name: Irofulven
• Synonyms: (R)-Irofulven;(-)-(HydroxyMethyl)acylfulvene;(6'R)-6'-Hydroxy-3'-(hydroxyMethyl)-2',4',6'-triMethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one;HMAF;MGI 114;NSC 683863;Irofulvene
• CAS NO: 158440-71-2
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30162
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 158440-71-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 127-129°
• Appearance: /
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Irofulven(CAS DataBase Reference)
• NIST Chemistry Reference: Irofulven(158440-71-2)
• EPA Substance Registry System: Irofulven(158440-71-2)

Safety Data

• Hazardous Substances Data: 158440-71-2(Hazardous Substances Data)

Usage

Uses

Semi-synrhetic antitumor agent derived from Illudin S. Inhibits DNA synthesis and induces apoptosis in tumor cells. Antineoplastic.

Upstream product

• 1149-99-1 illudin S 
• 50-00-0 formaldehyd 
• 33781-60-1 (R)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one 

Downstream Products

• 501426-42-2 6-ethyl-2,5,7-trimethyl-1-methylene-1H-inden-4-ol 

Relevant articles and documents

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.

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).

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.