Work

Total synthesis of diazaquinomycins H and J using double Knorr cyclization in the presence of triisopropylsilane

Year: 2019

Type: article

Abstract: selective amidation of diamine 6 with Meldrum's acid derivatives, subsequent EDC coupling with 3-oxobutanoic acid, followed by double Knorr cyclization in the presence of triisopropylsilane (TIPS). We found that the addition of TIPS was crucial to obtain pure diazaquinomycins H and J, while preventing isomerization of the terminal iso-branched tail in sulfuric acid. Our developed synthesis provided diazaquinomycins H (1) and J (2) in 8 steps from commercially available starting materials in 25% and 21% overall yields, respectively. The spectroscopic data of synthetic diazaquinomycins H (1) and J (2) agreed very favorably with those of reported natural products.

Source: RSC Advances

DOI: 10.1039/c8ra09792e

Authors: Allan M. Prior, Dianqing Sun

Institution: University of Hawaii at Hilo

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,042

Funders: Hawaii Community Foundation, National Institute of General Medical Sciences