NEW METHOD FOR PRODUCING NEPLANOCIN A AND INTERMEDIATE FOR THAT PURPOSE
PROBLEM TO BE SOLVED: To obtain Neplanocin A having strong carcinostatic action in a good yield by the short production process of reverse Diels-Alder reactions of an intermediate obtained from cyclopentadiene and 1,4-benzoquinone. SOLUTION: Neplanocin A is obtained by reacting a compound of formula...
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| creator | OGASAWARA KUNIRO YOSHIDA NAOYUKI |
| description | PROBLEM TO BE SOLVED: To obtain Neplanocin A having strong carcinostatic action in a good yield by the short production process of reverse Diels-Alder reactions of an intermediate obtained from cyclopentadiene and 1,4-benzoquinone. SOLUTION: Neplanocin A is obtained by reacting a compound of formula I (R and R are each H or a 2-20C alkanoyl) as a starting raw material with a halogenation agent, by protecting the hydroxyl group of the resultant product, by treating it with an oxidizing agent, by reacting the product with an acetalizing agent, by dehalogenation to obtain a compound of formula II (Y is a protecting group), by the reverse Diels-Alder reaction of the compound of formula II, by treating the resultant product with an oxidizing agent or the like, by O. Mitsunobu synthesis of the product and by deblocking. For example, the compound of formula I is new and is obtained by the transesterification of a racemate of formula III with an acylating agent in the presence of a hydrolase. Not only compound of formula II but also other intermediates in the above reaction are all new. |
| format | Patent |
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SOLUTION: Neplanocin A is obtained by reacting a compound of formula I (R and R are each H or a 2-20C alkanoyl) as a starting raw material with a halogenation agent, by protecting the hydroxyl group of the resultant product, by treating it with an oxidizing agent, by reacting the product with an acetalizing agent, by dehalogenation to obtain a compound of formula II (Y is a protecting group), by the reverse Diels-Alder reaction of the compound of formula II, by treating the resultant product with an oxidizing agent or the like, by O. Mitsunobu synthesis of the product and by deblocking. For example, the compound of formula I is new and is obtained by the transesterification of a racemate of formula III with an acylating agent in the presence of a hydrolase. Not only compound of formula II but also other intermediates in the above reaction are all new.</description><edition>7</edition><language>eng</language><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS ; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM ; BEER ; BIOCHEMISTRY ; CHEMISTRY ; ENZYMOLOGY ; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; MICROBIOLOGY ; MUTATION OR GENETIC ENGINEERING ; ORGANIC CHEMISTRY ; SPIRITS ; VINEGAR ; WINE</subject><creationdate>2000</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20000215&DB=EPODOC&CC=JP&NR=2000044514A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25563,76418</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20000215&DB=EPODOC&CC=JP&NR=2000044514A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>OGASAWARA KUNIRO</creatorcontrib><creatorcontrib>YOSHIDA NAOYUKI</creatorcontrib><title>NEW METHOD FOR PRODUCING NEPLANOCIN A AND INTERMEDIATE FOR THAT PURPOSE</title><description>PROBLEM TO BE SOLVED: To obtain Neplanocin A having strong carcinostatic action in a good yield by the short production process of reverse Diels-Alder reactions of an intermediate obtained from cyclopentadiene and 1,4-benzoquinone. SOLUTION: Neplanocin A is obtained by reacting a compound of formula I (R and R are each H or a 2-20C alkanoyl) as a starting raw material with a halogenation agent, by protecting the hydroxyl group of the resultant product, by treating it with an oxidizing agent, by reacting the product with an acetalizing agent, by dehalogenation to obtain a compound of formula II (Y is a protecting group), by the reverse Diels-Alder reaction of the compound of formula II, by treating the resultant product with an oxidizing agent or the like, by O. Mitsunobu synthesis of the product and by deblocking. For example, the compound of formula I is new and is obtained by the transesterification of a racemate of formula III with an acylating agent in the presence of a hydrolase. 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SOLUTION: Neplanocin A is obtained by reacting a compound of formula I (R and R are each H or a 2-20C alkanoyl) as a starting raw material with a halogenation agent, by protecting the hydroxyl group of the resultant product, by treating it with an oxidizing agent, by reacting the product with an acetalizing agent, by dehalogenation to obtain a compound of formula II (Y is a protecting group), by the reverse Diels-Alder reaction of the compound of formula II, by treating the resultant product with an oxidizing agent or the like, by O. Mitsunobu synthesis of the product and by deblocking. For example, the compound of formula I is new and is obtained by the transesterification of a racemate of formula III with an acylating agent in the presence of a hydrolase. Not only compound of formula II but also other intermediates in the above reaction are all new.</abstract><edition>7</edition><oa>free_for_read</oa></addata></record> |
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| subjects | ACYCLIC OR CARBOCYCLIC COMPOUNDS ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM BEER BIOCHEMISTRY CHEMISTRY ENZYMOLOGY FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE HETEROCYCLIC COMPOUNDS METALLURGY MICROBIOLOGY MUTATION OR GENETIC ENGINEERING ORGANIC CHEMISTRY SPIRITS VINEGAR WINE |
| title | NEW METHOD FOR PRODUCING NEPLANOCIN A AND INTERMEDIATE FOR THAT PURPOSE |
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