A Novel Conversion of Dibenzazecines into Homoerythrina Compounds : Synthesis of cis-16,17-Dimethoxyhomoerythrinan-3-one
スポンサーリンク
概要
- 論文の詳細を見る
Two dibenzazecine derivatives (8 and 9) were readily prepared as a mixture by a photochemical reaction of the bromophenolic compound (6). Reduction of the mixture (8 and 9) with diborane followed by column chromatography on silica gel gave the secondary amine (11), which was converted into the diene derivative (12) by Birch reduction. Treatment of 12 with 5% hydrochloric acid, followed by O-methylation with diazomethane provided the homoerythrina base (1) in 21% yield.On the other hand, the base (1) was also prepared via Birch reduction of the amine (9). The mixture of the amides (8 and 9) was reduced directly with sodium in liquid ammonia and subjected to fractional crystallization to yield 13. On treatment with 5% hydrochloric acid, 13 produced the homoerythrina derivative (14), which was methylated with diazomethane to afford 15. Finally, the homoerythrina base (1) was obtained by reduction of the amide group in 15.
- 社団法人日本薬学会の論文
- 1986-01-25
著者
-
田中 斉
Faculty Of Pharmacy Meijo University
-
伊藤 一男
Faculty of Pharmacy, Meijo University
-
高村 康
Faculty of Pharmacy, Meijo University
-
柴田 正芳
Faculty of Pharmacy, Meijo University
-
柴田 正芳
Faculty Of Pharmacy Meijo University
-
高村 康
Faculty Of Pharmacy Meijo University
-
伊藤 一男
Faculty Of Pharmacy Meijo University
関連論文
- Total Synthesis of a Xanthonolignoid, Kielcorin
- Total Synthesis of Silychristin, an Antihepatotoxic Flavonolignan
- A NEW FLAVANONE, NEOLINDERATONE, FROM LINDERA UMBELLATA THUNB. VAR. LANCEA MOMIYAMA
- Studies on the Flavonoid Components of Lindera umbellata THUNB. var. membranacea (MAXIM.) MOMIYAMA
- Total Synthesis of Coumarinolignans, Aquillochin (Cleomiscosin C) and Cleomiscosin D
- 2 Lindera属植物3種の新奇フラボノイド類の単離と構造(ポスター発表の部)
- Total Synthesis of Coumarinolignans, Propacin and Its Regioisomer
- TWO NOVEL FLAVANONES, METHYLLINDERATONE AND ISOLINDERATONE, FROM LINDERA UMBELLATA THUNB. VAR. MEMBRANACEA (MAXIM.) MOMIYAMA(Communications to the Editor)
- Total Synthesis of Daphneticin, a Coumarinolignoid
- A Novel Conversion of Dibenzazecines into Homoerythrina Compounds : Synthesis of cis-16,17-Dimethoxyhomoerythrinan-3-one
- 第10回ICHC(Tenth International Congress of Heterocyclic Chemistry)
- Total Synthesis of Cleomiscosin A, a Coumarinolignoid
- A NOVEL FLAVANONE, LINDERATONE, FROM LINDERA UMBELLATA
- Total Synthesis of (±)-Silybin, an Antihepatotoxic Flavonolignan
- A NOVEL DIHYDROCHALCONE, LINDERATIN FROM LINDERA UMBELLATA VAR. LANCEA
- A Novel Synthesis of cis-15,16-Dimethoxyerythrinan-3-one
- SYNTHESIS OF (±)-DYSAZECINE
- Synthesis of 3-Demethoxyerythratidinone via Formation of a Dibenzazonine Alkaloid
- カンツワブキFarfugium hiberniflorum(MAKINO)KITAM.の成分研究
- Studies on the Erythrina Alkaloids. XII. Conversion of Erysodienone Methiodide and Erysodienol to Dibenzazonine Derivatives
- Constituents of Rosaceous Plants. I. Structures of New Triterpenoids from Cowania mexicana
- Structural Elucidation and Chemical Conversion of Amorphispironone, a Novel Spironone form Amorpha fruticosa, to Rotenoids
- Isolation and Structure Determination of 4-O-Tigloyl-11,13-dihydro-autumnolide, a New Sesquiterpene Lactone from North Carolina Helenium autumnale L.
- Four Euglobals from Eucalyptus blakelyi
- Structures of Euglobals-G1,-G2,-G3,-G4,and -G5 from Eucalyptus gradis
- Euglobal-In-1,a New Euglobal from Eucalyptus incrassata
- Studies on the Constituents of Leguminous Plants. XII. : The Structures of New Triterpenoid Saponins from Wistaria branchybotrys SIEB. et ZUCC.
- Studies on the Constituents of Marsdenia formosana MASAMUNE. IV. Photochemical Reaction of Marsformoxide A
- Studies on the Constituents of Marsdenia formosana MASAMUNE. III. : Isolation and Structural Elucidation of Some New Steroidal Glycosides
- Studies on the Constituents of Marsdenia formosana MASAMUNE. II. Structures of Marsformoxide A and Marsformoxide B
- Erythrinaアルアロイド研究(第3報)Erythrina X bidwillii LINDL.のアルカロイド その3 新塩基Erybidineの構造
- Studies on the Constituents of Leguminous Plants. XI. : The Structures of New Triterpenoids from Wistaria brachybotrys SIEB. et ZUCC.
- Obovatol and Obovatal, Novel Biphenyl Ether Lignans from the Leaves of Magnolia obovata THUNB.
- Structure and Conformation of Eupafortunin, a New Germacrane-Type Sesquiterpene Lactone from Eupatorium fortunei TURCZ(Pharmacognosy,Chemical)
- BALANOPHONIN, A NEW NEO-LIGNAN FROM BALANOPHORA JAPONICA MAKINO
- Studies on the Erythrina Alkaloids. XI. Alkaloids of Erythrina crystagalli LINN. Structure of a New Alkaloid, Crystamidine
- Studies on the Syntheses of Indoline Derivatives from N-Sulfonamides
- Separation of L- and D-Amino Acids as Diastereomeric Derivatives by High Performance Liquid Chromatography
- 1-Phenethyl-, およびl-Styryl-1,2,3,4-tetrahydroisquinoline型化合物のNMRスペクトルについて
- Studies on the Constituents of Marsdenia formosana MASAMUNE. V. Isolation and Structure of a New Triterpenoid, Marsformosanone
- Syntheses of 1,2,3,4-Tetrahydroisoquinolines from N-Sulfonyl-phenethylamines and Aldehydes
- Studies on the Erythrina Alkaloids. VIII. Alkaloids of Erythrina X bidwillii LINDL. (4). Synthesis of Erybidine by Photochemical Reaction
- Erythrinaアルカロイド研究(第2報)Erythrina X bidwillii LINDL.のアルカロイド その2 新塩基Erythrinineの構造
- Erythrinaアルカロイド研究(第1報)Erythrina X bidwillii LINDL.のアルカロイド その1 塩基の単離, および同定
- Structure of Erybidine, a New Alkaloid from Erythrina xbidwilli LINDL.
- 1-Phenethyl-, 1-Styryl-および1-Isopentyl-1,2,3,4-tetrahydroisoquinoline型化合物の合成