The Reductive Fragmentation of 7‐Hydroxy‐9,10‐dioxotaxoids | Zendy

Appendino Giovanni | Zendy; covich Alain | Zendy; Bettoni Piergiorgio | Zendy; Dambruoso Paolo | Zendy; Sterner Olov | Zendy; Fontana Gabriele | Zendy; Bombardelli Ezio | Zendy

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The Reductive Fragmentation of 7‐Hydroxy‐9,10‐dioxotaxoids

Author(s) -

Appendino Giovanni,

covich Alain,

Bettoni Piergiorgio,

Dambruoso Paolo,

Sterner Olov,

Fontana Gabriele,

Bombardelli Ezio

Publication year - 2003

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300376

Subject(s) - chemistry , aldol reaction , fragmentation (computing) , cerium , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , catalysis , computer science , operating system

The retro‐aldol reductive fragmentation of different structural types of 7‐hydroxy‐9,10‐dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium( III ) promotion with NaBH 4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8‐ seco ‐taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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