Synthetic Studies on Camptothecins. Part 1 | Zendy

Zhang LiPeng | Zendy; Bao Yong | Zendy; Kuang YunYan | Zendy; Chen FenEr | Zendy

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Synthetic Studies on Camptothecins. Part 1

Author(s) -

Zhang LiPeng,

Bao Yong,

Kuang YunYan,

Chen FenEr

Publication year - 2008

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200890218

Subject(s) - chemistry , tricyclic , yield (engineering) , hydroxylation , camptothecin , lactone , pyridine , enantioselective synthesis , stereochemistry , total synthesis , organic chemistry , combinatorial chemistry , catalysis , enzyme , materials science , metallurgy

A six‐step asymmetric total synthesis of (20 S )‐camptothecin ( 1 ) has been accomplished in 25% overall yield starting from the known pyridone 3 . The key steps in this synthesis are the chemoselective Ni‐catalyzed hydrogenation of 3‐cyanopyridone 6 to 3‐formylpyridone 7 in AcOH/pyridine/H 2 O and the Davis asymmetric hydroxylation of tricyclic lactone 4 utilizing a chiral N ‐sulfonyloxaziridine into (4′ S )‐tricyclic hydroxylactone 2 .

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