Total Synthesis of a Pyrroloindoloquinazoline Alkaloid

A highly concise stereoselective synthesis of a newly identified alkaloid with a pyrroloindoloquinazoline skeleton has been achieved. To this end, a chiral auxiliary mediated asymmetric acetate aldol reaction on tryptanthrin was explored and the resulting adduct was converted to the product by a nov...

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Bibliographic Details
Published in	Organic letters Vol. 15; no. 15; pp. 3942 - 3945
Main Authors	Gahtory, Digvijay, Chouhan, Mangilal, Sharma, Ratnesh, Nair, Vipin A
Format	Journal Article
Language	English
Published	WASHINGTON American Chemical Society 02.08.2013 Amer Chemical Soc
Subjects	acetates alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry boron compounds chemical reactions chemical structure Chemistry Chemistry, Organic chlorides Cyclization Indoles - chemical synthesis Indoles - chemistry methanol Molecular Structure nickel Physical Sciences Pyrroles - chemical synthesis Pyrroles - chemistry Quinazolines - chemical synthesis Quinazolines - chemistry Science & Technology Stereoisomerism stereoselective synthesis HYDROGENOLYSIS STEREOREGULATIONS ONE-POT SYNTHESIS ANALOGS C-O BONDS ALDOL REACTIONS ARYL ETHERS TRYPTANTHRIN
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ISSN	1523-7060 1523-7052 1523-7052
DOI	10.1021/ol401709t

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Summary:	A highly concise stereoselective synthesis of a newly identified alkaloid with a pyrroloindoloquinazoline skeleton has been achieved. To this end, a chiral auxiliary mediated asymmetric acetate aldol reaction on tryptanthrin was explored and the resulting adduct was converted to the product by a novel one-pot reductive cyclization/transamidation using NiCl2·6H2O/NaBH4 in methanol.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052 1523-7052
DOI:	10.1021/ol401709t