Process for the synthesis of optically active anthracyclines

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Reexamination Certificate

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C568S308000, C536S006400, C536S018500

Reexamination Certificate

active

06921841

ABSTRACT:
It is described a process for the synthesis of optically active anthracyclines by the fact that the key intermediate (R)2-acetyl-2-hydroxy-1,2,3,4-tetrahydronaphtalene 5,8-dialkoxy-3,4-dihydronaphtalene by acylation asymmetric dihydroxylation, transformation into chloroacetate, dehydrochloridation and final hydrolysis.

REFERENCES:
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patent: 4405713 (1983-09-01), Fujiwara et al.
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XP002188593, Tanno, Norihiko et al., “Preparation of dihydroxytetrahyrdronaphthacenedione derivatives as intermediates for anthracycline antibiotics,” Sumitomo Pharmaceuticals Co., Ltd., Japan, Jun. 16, 1987.
XP002188355, Nakajima, M. et al., “Short-Step Asymmetric Synthesis of Anthracycline Antibiotics via Enantioselective Dihydroxylation by Osmium Tetroxide with Chiral Diamine,” Tetrahedron, vol. 49, No. 47, 1993, pp. 10807-10816.
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