抄録
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.
| 元の言語 | English |
|---|---|
| ページ（範囲） | 2305-2310 |
| ページ数 | 6 |
| ジャーナル | Synthesis (Germany) |
| 巻 | 51 |
| 発行部数 | 11 |
| DOI | |
| 出版物ステータス | Published - 2019 1 1 |
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ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
これを引用
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.
：: Synthesis (Germany), 巻 51, 番号 11, 01.01.2019, p. 2305-2310.研究成果: Article
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TY - JOUR
T1 - Bioinspired Synthesis of the Central Core of Halichonadin H
T2 - The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products
AU - Ichikawa, Yoshiyasu
AU - Yamasaki, Toshiki
AU - Nakanishi, Keisuke
AU - Udagawa, Yutaro
AU - Hosokawa, Seijiro
AU - Masuda, Toshiya
PY - 2019/1/1
Y1 - 2019/1/1
N2 - 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.
AB - 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.
KW - biosynthesis
KW - isocyanides
KW - marine natural products
KW - Passerini reaction
KW - terpenes
UR - http://www.scopus.com/inward/record.url?scp=85065886924&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85065886924&partnerID=8YFLogxK
U2 - 10.1055/s-0037-1610867
DO - 10.1055/s-0037-1610867
M3 - Article
AN - SCOPUS:85065886924
VL - 51
SP - 2305
EP - 2310
JO - Synthesis (Germany)
JF - Synthesis (Germany)
SN - 0039-7881
IS - 11
ER -