S. Fazal Hussain

Feruloyltyramine from Hypecoum

Abstract Feruloyltyramine amide has been isolated from Hypecoum parviflorum and from H. imberbe .

Oxyhydrastinine, an isoquinolone alkaloid from the papaveraceae

Abstract The new isoquinolone, oxyhydrastinine, has been obtained from Argemone mexicana and from Papaver dubium var. glabrum (Papaveraceae).

Revised structure for fumarofine, an indenobenzazepine type alkaloid

Fumarofine is not a spirobenzylisoquinoline. Rather, it is the first know reduced indenobensazepine alkaloid, and possesses the cis B/C fused structure 7. Rearrangement of synthetic spirobensylisoquinoline 12 using methanesulfonyl chloride furnished indenobensazepine 14. Osmium tetroxide oxidation of 14 gave cis-glysol 15. O-Methylfumarofine (8) was then obtained through pyridinium chlorochromate oxidation of 15.

A new group of isoquinoline alkaloids : The secoberbines

Abstract The new isoquinoline alkaloid (−)-peshawarine ( 1 ) has been isolated from Hypecoum parviflorum Kar. & Kir. (Papaveraceae). Its synthesis in the racemic form from coptisine ( 6b ) involves a novel approach to cyclic hemiacetals in which the key step is the transformation of the aldehyde (±)-aobamine ( 10b ) into the hemiacetal 12b using ethyl chloroformate. (±)-Corydalisol ( 11b ) and (±)-canadaline ( 10a ) have also been synthesized for the first time. The absolute configuration of (−)-1 was determined by chemical correlation with (+)-rhoeagenine methiodide ( 20 ). The chirality of the alkaloid (+)-canadaline ( 10a ) has also been established by analogy to (+)-corydalisol ( 11b ). (−)-Peshawarine ( 1 ), (+)-canadaline ( 10a ), (+)-corydalisol ( 11b ), and aobamine ( 10b ), as well as hypecorine ( 22 ) and hypecorinine ( 23 ), are members of a new group of isoquinoline alkaloids, the secoberbines.

The photochemistry of proaporphines: a new route to the aporphines

Abstract Proaporphines undergo light catalyzed rearrangement. Pakistanamine ( 1 ) is thus converted into lumipakistanine ( 2 ), while pronuciferine ( 7 ) and N-acetylnorpronuciferine ( 8 ) afford the corresponding C-9 hydroxylated aporphines 9 and 10 . Possible biogenetic schemes for the formation of C-8, C-9-, and C-8,9-substituted aporphines are presented.

Kalashine, a novel type aporphine-benzylisoquinoline alkaloid

Abstract Berberis orthobotrys produces the new dimer kalashine ( 1 ), together with the previously reported pakistanamine ( 2 ) and pakistanine ( 3 ). Kalashine is the first aporphine-benzylisoquinoline known to be substituted at C-11. Acid catalyzed rearrangement of pakistanamine ( 2 ) in 3N HCl leads to 1-0-methylpakistanine ( 6 ) together with small amounts of 1-0-methylkalashine ( 7 ) and (+)-armepavine ( 8 ). Rearrangement of 2 using methanol containing a little 3N HCl gives about equal amounts of 6 and 1,10-di-O-methylpakistanine ( 9 ).

Parviflorine, a glycosidic spirobenzylisoquinoline alkaloid

Abstract (+)-Parviflorine ( 1 ), found in Fumaria parviflora Lam. (Fumariaceae), is the first known glycosidic spirobenzylisoquinoline alkaloid. Its acid hydrolysis yields (+)-parfumine ( 4 ) and D-glucose. Klynes rule indicates that 1 is a β-D-glucoside. The absolute configuration shown in expressions 1-11 is predominant among spirobenzylisoquinolines. A generalization has been drawn between plant source and the oxygenation pattern of ring C for the spirobenzylisoquinoline alkaloids.

A new class of isoquinoline alkaloids: The indenobenzazepines

Abstract The dark yellow indenobenzazepine alkaloids lahorine ( 1 ) and lahoramine ( 2 ) have been found in Fumaria parviflora Lam. (Fumariaceae). In a transformation with biogenetic implications, treatment of the spirobenzylisoquinolines dihydrofumariline ( 4 ) and dihydroparfumidine ( 7 ) with methanesulfonyl chloride and triethylamine in dry THF, followed by iodine oxidation, provided 1 and 2 , respectively.

Khyberine and the biogenesis of dimeric aporphine-benzylisqoquinoline alkaloids

Abstract The new aporphine-benzylisquinoline khyberine ( 4b ) is present in Berberis calliobotrys Aitch. ex Bienert in about one part per million. An effort is made to present a complete scheme for the biogenesis of aporphine-benylisoquinoline dimers which arise from the condensation of two coclaurine units.