Exploring the functionalisation of the thieno[2,3- d ]pyrimidinedione core: Late stage access to highly substituted 5-carboxamide-6-aryl scaffolds

O’Rourke, Kerry M.; Johnstone, Erin S.; Becker, Holger M.; Pimlott, Sally L.; Sutherland, Andrew

doi:10.1016/j.tet.2018.06.019

Cited by 5 publications

(1 citation statement)

References 24 publications

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“…Many compounds contain pyrimidine as their core motif, such as pyrrolo[2,3- d ]pyrimidine or thieno[2,3- d ]pyrimidine, and show diverse biological activities including antitumor, antiviral, analgesic, antiproliferative, antipyretic, and anticancer . Similarly, various biologically active pyrimidinediones represented by thieno[2,3- d ]pyrimidinedione are effective antihypertensive agents that control systolic blood pressure . In addition, 5,6-dihydrouracil as the reduced form of pyrimidinedione also attracted attention, which is exemplified by the FDA-approved drug dasabuvir .…”

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confidence: 99%

Total Synthesis and Stereochemical Revision of Biemamides B and D

Srivastava

Macha

2019

Org. Lett.

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The first expedient asymmetric synthesis of both enantiomers of 5,6-dihydrouracil-type marine natural products biemamides B and D was achieved from chiral 1-(α-methylbenzyl)aziridine-2-carboxylate. The key steps involved in the synthetic route are regio- and stereoselective aziridine ring opening via azide followed by a base-induced cyclization reaction. After comparison of ECD and optical rotation data of both synthetic enantiomers, the absolute configuration of natural biemamides B and D at the C5 position has been assigned as (−)-(5S), which is an enantiomer to the originally proposed structure (−)-(5R).

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