1446348-69-1Relevant articles and documents
Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products
Ichikawa, Yoshiyasu,Yamasaki, Toshiki,Nakanishi, Keisuke,Udagawa, Yutaro,Hosokawa, Seijiro,Masuda, Toshiya
, p. 2305 - 2310 (2019)
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.
A biomimetic approach to terpenes isolated from marine sponges: A Ugi coupling reaction in a hypothetical biosynthesis
Saito, Kenta,Nishimori, Ayumu,Kotsuki, Hiyoshizo,Nakano, Keiji,Ichikawa, Yoshiyasu
, p. 757 - 761 (2013/05/09)
A unique pathway for the biosynthesis of marine sponge terpenes is proposed. Based on this proposal, a biomimetic approach using a Ugi coupling reaction has been designed and applied to the efficient construction of the right-side, peptide-like portions of boneratamides and exigurin. Georg Thieme Verlag Stuttgart - New York.