Asymmetric Synthesis of Nabscessin A from Inositol and d-Camphor.

Autor:	Wu HY; Department of Chemistry, National Central University, No. 300 Jhong-Da Road, Jhong-li, Taoyuan 32001 Taiwan., Wang WY; Department of Chemistry, National Central University, No. 300 Jhong-Da Road, Jhong-li, Taoyuan 32001 Taiwan., Feng CC; Department of Chemistry, National Central University, No. 300 Jhong-Da Road, Jhong-li, Taoyuan 32001 Taiwan., Hou DR; Department of Chemistry, National Central University, No. 300 Jhong-Da Road, Jhong-li, Taoyuan 32001 Taiwan.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2020 Oct 16; Vol. 85 (20), pp. 13153-13159. Date of Electronic Publication: 2020 Sep 25.
DOI:	10.1021/acs.joc.0c01839
Abstrakt:	An enantiomer of nabscessin A ( 1 ), an aminocyclitol amide with antimicrobial activity, was synthesized from myo -inositol and dimethyl d-camphor acetal in 14 steps. Formal synthesis of natural nabscessin A was also achieved through the new approach to access both enantiomers of 4,5-di- O -benzyl- myo -inositol, derived from the same set of starting materials. This synthesis features utilizations of the existing framework of myo -inositol and a regioselective esterification.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu