A Concise and Convergent Synthesis of Luotonin B and E

Abstract A concise and highly convergent practical synthesis of topoisomerase 1 inhibitor luotonin B was developed in a one-pot process in excellent yields. The C and D rings of luotonin B was constructed by cascade cyclizations of 2-cyanoquinoline-3-aldehyde or 2-cyanoquinoline-3-hemiacetal with me...

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Bibliographic Details
Published in:Synlett 2011-01, Vol.2011 (1), p.84-88
Main Authors: Wagh, Manoj Balu, Shankar, R., Kumar, U. K., Gill, C. H.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
letter
Organic chemistry
Preparations and properties
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Summary:Abstract A concise and highly convergent practical synthesis of topoisomerase 1 inhibitor luotonin B was developed in a one-pot process in excellent yields. The C and D rings of luotonin B was constructed by cascade cyclizations of 2-cyanoquinoline-3-aldehyde or 2-cyanoquinoline-3-hemiacetal with methylanthranilate under acidic conditions. The luotonin B was then converted into luotonin E by an acid-catalyzed etherification reaction.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259098