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Regioselective Quinazolinone-Directed Ortho Lithiation of Quinazolinoylquinoline: Practical Synthesis of Naturally Occurring Human DNA Topoisomerase I Poison Luotonin a and Luotonins B and E

Regioselective Quinazolinone-Directed Ortho Lithiation of Quinazolinoylquinoline: Practical Synthesis of Naturally Occurring Human DNA Topoisomerase I Poison Luotonin a and Luotonins B and E

Santosh B Mhaske, Narshinha P Argade

J Org Chem. 2004 Jun 25;69(13):4563-6.

PMID: 15202923

Abstract:

A regioselective quinazolinone-directed ortho lithiation on an adjacent quinoline moiety has been used as a key step for a short, efficient, and practical synthesis of the human DNA topoisomerase I poison luotonin A and luotonins B and E. The quinazolinoylquinoline 5 on treatment with in situ-generated nonnucleophilic mesityllithium furnished the desired dilithiated intermediate 6, which on treatment with formaldehyde followed by Mitsunobu ring closure reaction gave luotonin A (1a) in very good yield. The reaction of dilithiated intermediate 6 with DMF directly furnished luotonin B (1b) in 81% yield. Luotonin B (1b) on methylation with p-TSA/methanol gave luotonin E (1c) in 82% yield.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP205989135	Luotonin B		205989-13-5	Price
AP244616840	Luotonin E		244616-84-0	Price

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