Abstract
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.
Original language | English |
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Pages (from-to) | 2305-2310 |
Number of pages | 6 |
Journal | Synthesis (Germany) |
Volume | 51 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2019 |
Keywords
- Passerini reaction
- biosynthesis
- isocyanides
- marine natural products
- terpenes
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry