Formation of 3,4‐Diarylpyrrole‐ and Pyrrolocoumarin Core of Natural Marine Products via Barton–Zard Reaction and Selective O‐Demethylation

Formation of 3,4‐Diarylpyrrole‐ and Pyrrolocoumarin Core of Natural Marine Products via Barton–Zard Reaction and Selective O‐Demethylation Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2020, Volume: 2020, Number: 14, Pages: 2093-2100 Pages count : 8 DOI: 10.1002/ejoc.202000099

Authors

Silyanova Eugenia A. ¹ , Samet Alexander V. ¹ , Salamandra Lev K. ¹ , Khrustalev Victor N. ^1,2 , Semenov Victor V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
2	Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russian Federation

A metal-free approach to 3,4-diarylpyrrole-2-carboxylate and pyrrolocoumarin cores of lamellarins and related natural products based on Barton–Zard reaction of nitrostilbenes with ethyl isocyanoacetate was developed. In the case of diarylpyrrole-2-carboxylates with a 3-(o-methoxyphenyl) fragment, treatment with 1 equiv. of. BBr3 resulted in selective O-demethylation of the ortho-methoxy group, while other methoxy groups in the molecule remained intact. The resulting 3-(2-hydroxyphenyl)pyrrole-2-carboxylates underwent base-induced lactonization to form the target pyrrolocoumarins.

Silyanova E.A. , Samet A.V. , Salamandra L.K. , Khrustalev V.N. , Semenov V.V.
Formation of 3,4‐Diarylpyrrole‐ and Pyrrolocoumarin Core of Natural Marine Products via Barton–Zard Reaction and Selective O‐Demethylation
European Journal of Organic Chemistry. 2020. V.2020. N14. P.2093-2100. DOI: 10.1002/ejoc.202000099 WOS Scopus OpenAlex

Web of science:	WOS:000525867700010
Scopus:	2-s2.0-85081960793
OpenAlex:	W3007077860

DB	Citing
OpenAlex	28
Scopus	26
Web of science	25