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1

Synteza idarubicynonu. Inwersja konfiguracji na C-9 w epimerze (9R) syntonu pierścieni AB

Szechner B., Achmatowicz O., Bodalski R., Koszuk J.

Przemysł Chemiczny

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2006

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T. 85, nr 5

333-337

PL

Opracowano warunki inwersji konfiguracji trzeciorzędowej grupy hydroksylowej w syntonie pierścieni AB idarubicynonu.

EN

Waste 3-acetyl-5,8-dimetoxy-3-hydroxy-3,4-dihydro-2Hnaphthalene-1-spiro-2’-1’-3’-dithiolane 4, a 7:3 mixture of (R) and (S) enantiomers on boiling with ethyl acetate afforded hydroxyketone (R)-4 with high enantiomeric purity (ca. 96%). A two-step inversion of the stereogenic center in the latter gave hydroxyketone (S)-4 in 40% yield. The overall yield of (S)-4, an advanced intermediate in the synthesis of idarubicinone, was thus raised by about 10%.

2

Syntezy naturalnych i modyfikowanych antybiotyków antracyklinowych ze wspólnego prekursora : 3,4-DI-0-acetylo-L-ramnalu

Grynkiewicz G., Achmatowicz O., Fokt I., Priebe W., Ramza J., Szechner B., Szeja W.

Wiadomości Chemiczne

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2002

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[Z] 56, 7-8

535-560

EN

While natural anthracycline antibiotics retain their position of clinically important antitumor drugs despite of serious side effects, much effort is directed towards their improvement by rational structural changes. Most of useful anthracycline antibiotics chemistry is done by dissconnection - modification approach, folloved by de novo glycosidic bond assembly. It is pointed out that 1,2- and 2,3-unasturated pyranosides constitute an important class of intermediates, useful for synthesis of natural and modified antibiotic aminosugars. Glycals derived from 3-amino-2,3,6-trideoxypyranoses and their 1-O-silylated derivatives are useful glycosyl donors for a variety of alcohols. Also anthracycline antibiotics can be obtained from them in simple preparative procedures which are amenable for scale up and technical process development. Moreover, unsaturated pyranoses from 6-deoxy-L- configurational series are useful chiral precursors for anthracycline aglycons synthesis. Remarkably, various synthetic schemes comprising anthracycline antibiotic sugars, aglycons and new synthetic analogues can be traced down to the single common precursor: 3,4-di-O-acetyl-L-rhamnal, easily obtained from a commodity chemical (raw material in food industry) L-rhamnose.

3

Total Synthesis of Both Enantiomers of Daunosamine and Ristosamine

Szechner B., Achmatowicz O., Badowska-Rosłonek K.

Polish Journal of Chemistry

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1999

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vol. 73 nr 7

1133-1141

EN

Efficient, enentioselective syntheses of the title 3-amino-2,3,6-trideoxyhexoses from non-carbohydrate precursors, (S)- and (R)-1-(2-furyl)ethanol, readily available by enzyme-mediated kinetic resolution, are described.

4

Synthesis of Kedarosamine, a Sugar Portion of the Chromoprotein Antibiotic Kedarcidine

Priebe W., Skibicki P., Neamati N., Achmatowicz O., Grynkiewicz G., Szechner B.

Polish Journal of Chemistry

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1999

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vol. 73 nr 7

1143-1152

EN

Synthesis of the sugar portion (kedarosamine) of a recently discovered chromoprotein antitumor antibiotic and spiroketal-macrolide A82548A is described. Kedarosamine was prepared from readily available methyl A-L-rhamnoside. This route can also be used to prepare different glycosyl donors and analogues of kedarosamine potentially useful in the synthesis of biologically important congeners.