Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea | Zendy

Pengcheng Yan | Zendy; Ge Li | Zendy; Chaojie Wang | Zendy; Jianzhang Wu | Zendy; Zhongmin Sun | Zendy; Gary E. Martin | Zendy; Xiao Wang | Zendy; Mikhail Reibarkh | Zendy; Josep Saurí | Zendy; Kirk R. Gustafson | Zendy

Open Access

Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea

Author(s) -

Pengcheng Yan,

Ge Li,

Chaojie Wang,

Jianzhang Wu,

Zhongmin Sun,

Gary E. Martin,

Xiao Wang,

Mikhail Reibarkh,

Josep Saurí,

Kirk R. Gustafson

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b02856

Subject(s) - stereocenter , chemistry , alkaloid , two dimensional nuclear magnetic resonance spectroscopy , antioxidant , carbon 13 nmr , stereochemistry , computational chemistry , organic chemistry , catalysis , enantioselective synthesis

The challenging structural motif of dictyospiromide ( 1 ), a spirosuccinimide alkaloid with antioxidant properties that are associated with activation of the Nrf2/ARE signaling pathway, was assigned using contemporary NMR experiments complemented with anisotropic NMR, chiroptical, and computational methodologies. Anisotropic NMR parameters provided critical orthogonal verification of the configuration of the difficult to assign spiro carbon and the other stereogenic centers in 1 .

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