Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products

Autor:	Seijiro Hosokawa, Yutaro Udagawa, Toshiki Yamasaki, Yoshiyasu Ichikawa, Toshiya Masuda, Keisuke Nakanishi
Rok vydání:	2019
Předmět:	010405 organic chemistry Stereochemistry Isocyanide Organic Chemistry 010402 general chemistry 01 natural sciences Catalysis Passerini reaction 0104 chemical sciences Terpene chemistry.chemical_compound Reaction sequence chemistry Biosynthesis Structural motif Acetamide
Zdroj:	Synthesis. 51:2305-2310
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0037-1610867
Popis:	A pathway is proposed for the biosynthesis of the unique homodimeric terpene, halichonadin H. The proposed biosynthetic pathway involves two key Passerini reactions of eudesmane-type terpene isocyanides. The Passerini reaction of a model terpene isocyanide and formaldehyde afforded an α-hydroxy acetamide, which was further subjected to oxidation and a second Passerini reaction. This reaction sequence furnished an α-hydroxy malonamide connected with two identical terpene units which is the identical structural motif found in halichonadin H.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::72ef5c41ab8cbd63b50e5c8368c2b6e8 https://doi.org/10.1055/s-0037-1610867 Zobrazit plný text záznamu