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3 Polish Journal of Chemistry

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Synthesis of Isoquinoline Alkaloid, (š)-Salsolidine, Using Thiazolino[2,3-a]isoquinolinone S-Oxide as Intermediate

100%

Rozwadowska M. D. , Sulima A.

tom Vol. 75, nr 12

1847-1852

Thiazolino[2,3-a]isoquinolinones have been oxidized to the corresponding S-oxides and their 10b-methyl derivatives desulfurized with Raney nickel to give (š) N-acyl salsolidine. Base-catalyzed hydrolysis of the N-acetyl derivative afforded (š)-salsolidine. C-Methylation reactions of the title heterocyclic system have been investigated throughly. Stereochemistry ofthe synthesized compounds nas been established.

The structure of 7,8-dimethoxy-3-oxo-3a,4,5,9b-tetrahydroisoquinolino-[1,2b]thiazolidine

100%

Kosturkiewicz Z. , Sulima A.

tom Vol. 72, nr 11

2500-2503

The crystal structure of 7,8-dimethoxy-3-oxy-3a,4,5,9b-tetrahydroisoquinolino-[1,2b]thiazolidine has been investigated by X-ray diffraction methods. Crystals are monoclinic, space group P2-1/c, a=19.789(2), b=7.454(1), c=8.917 A, beta=100.43(1) degree, Z=4. The structure was solved by direct methods and refined to R=0.0329 for 2110 observed reflections. The sum of three bond angles around N atom is 359.3(3) degree, showing is near planar surrounding. The tetrahydroisoquinoline moiety is composed of the planar aromatic ring and hydrogenated heterocyclic ring having the conformation of non-ideal sofa. The next condensed heterocyclic five-membered ring accepts the form of envelope. This is the first published crystal structure of tetrahydroisoquinoline moiety fused with sulfur containing five-membered ring.

Total synthesis of (+)- and (-)-corydalisol

80%

Chrzanowska M. , Józkowiak J. , Rozwadowska M. D. , Sulima A.

tom Vol. 72, nr 11

2399-2404

The first total synthesis of enantiomerically enriched (+)- and (-)-corydalisol (1) has been performed by addition of lithiated optically pure 1,3-dithiane 3b to hydrastinine chloride (2a), followed by desulfurization, separation of diastereomers and reduction with lithium aluminum hydride.