PRODUCTION OF HYMENIALDISINE, ITS DERIVATIVE AND THEIR SYNTHETIC INTERMEDIATE AND SYNTHETIC INTERMEDIATE

• Main Authors: ANURA YOUICHI, TATSUOKA TOSHIO
• Format: Patent
• Language: English
• Published: 28.11.1995
• Edition: 6
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

PURPOSE:To enable total chemical synthesis of a hymenialdisine(derivative) having antitumor activity and expected to be usable as an improving and curing agent for cerebral ischemic disorder, ischemic cardiopathy, hypertension, arteriosclerosis, etc., by using a specific compound as a starting raw material. CONSTITUTION:A Z-configuration compound of a hymenialdisine(derivative) of formula VI is produced by reacting a compound of formula I (R is trimethylsilylethoxymethyl, etc.; R is trimethylsilylethoxymethyl, etc.; X is a halogen, etc.) synthesized from a pyrrole-2-carboxylic acid(derivative) and aldisine with a compound of formula, (R'O)2POCH2CO2R (R' is a 1-4C alkyl, etc.; R is a l-4C alkyl), converting the obtained compound of formula II into a compound of formula III with an oxidizing agent, reacting the product with an alkylsulfonyl halide, etc., reacting the produced compound of formula IV (R is an alkylsulfonyloxy, etc.) with guanidine to obtain a compound of formula V and finally deprotecting the product. The compound of formula II can be converted to a compound of formula IV (R is a halogen) with a halogenation agent.