期刊
ORGANIC LETTERS
卷 21, 期 22, 页码 8992-8996出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03394
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资金
- National Research Foundation of Korea (Centre for New Directions in Organic Synthesis) [NRF-2012M3A7B4049645, 2014R1A5A1011165]
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-(alpha-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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