Abstract
Total syntheses of two homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine, are described. Photocycloaddition of a dioxopyrrolobenzazepine to 1-methoxy-3-trimethylsilyloxybutadiene afforded, in a regio- and stereo-specific manner, the cyclobutane derivative, which was converted to a homoerythrinan derivative by utilizing a TBAF-induced 1,3-anionic rearrangement. The product was transformed into the title alkaloids in several steps.
| Original language | English |
|---|---|
| Pages (from-to) | 500-508 |
| Number of pages | 9 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 44 |
| Issue number | 3 |
| Publication status | Published - 1996 Mar |
| Externally published | Yes |
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Keywords
- 1,3-anionio rearrangement
- 3-epischelhammericine, [2 + 2]photo-cyclo-addition
- Homoerythrinan alkaloid
- Schelhammericine
- Total synthesis
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
- Drug Discovery
- Pharmacology
Cite this
Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine. / Tsuda, Yoshisuke; Ohshima, Takeshi; Hosoi, Shinzo; Kaneuchi, Satomi; Kiuchi, Fumiyuki; Toda, Jun; Sano, Takehiro.
In: Chemical and Pharmaceutical Bulletin, Vol. 44, No. 3, 03.1996, p. 500-508.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine
AU - Tsuda, Yoshisuke
AU - Ohshima, Takeshi
AU - Hosoi, Shinzo
AU - Kaneuchi, Satomi
AU - Kiuchi, Fumiyuki
AU - Toda, Jun
AU - Sano, Takehiro
PY - 1996/3
Y1 - 1996/3
N2 - Total syntheses of two homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine, are described. Photocycloaddition of a dioxopyrrolobenzazepine to 1-methoxy-3-trimethylsilyloxybutadiene afforded, in a regio- and stereo-specific manner, the cyclobutane derivative, which was converted to a homoerythrinan derivative by utilizing a TBAF-induced 1,3-anionic rearrangement. The product was transformed into the title alkaloids in several steps.
AB - Total syntheses of two homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine, are described. Photocycloaddition of a dioxopyrrolobenzazepine to 1-methoxy-3-trimethylsilyloxybutadiene afforded, in a regio- and stereo-specific manner, the cyclobutane derivative, which was converted to a homoerythrinan derivative by utilizing a TBAF-induced 1,3-anionic rearrangement. The product was transformed into the title alkaloids in several steps.
KW - 1,3-anionio rearrangement
KW - 3-epischelhammericine, [2 + 2]photo-cyclo-addition
KW - Homoerythrinan alkaloid
KW - Schelhammericine
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=0029989581&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0029989581&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0029989581
VL - 44
SP - 500
EP - 508
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 3
ER -