Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine

Yoshisuke Tsuda; Takeshi Ohshima; Shinzo Hosoi; Satomi Kaneuchi; Fumiyuki Kiuchi; Jun Toda; Takehiro Sano

doi:10.1248/cpb.44.500

Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine

Yoshisuke Tsuda, Takeshi Ohshima, Shinzo Hosoi, Satomi Kaneuchi, Fumiyuki Kiuchi, Jun Toda, Takehiro Sano

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

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
DOIs	https://doi.org/10.1248/cpb.44.500
Publication status	Published - 1996 Mar
Externally published	Yes

Keywords

1,3-anionio rearrangement
3-epischelhammericine, [2 + 2]photo-cyclo-addition
Homoerythrinan alkaloid
Schelhammericine
Total synthesis

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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title = "Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine",

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.",

keywords = "1,3-anionio rearrangement, 3-epischelhammericine, [2 + 2]photo-cyclo-addition, Homoerythrinan alkaloid, Schelhammericine, Total synthesis",

author = "Yoshisuke Tsuda and Takeshi Ohshima and Shinzo Hosoi and Satomi Kaneuchi and Fumiyuki Kiuchi and Jun Toda and Takehiro Sano",

year = "1996",

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doi = "10.1248/cpb.44.500",

language = "English",

volume = "44",

pages = "500--508",

journal = "Chemical and Pharmaceutical Bulletin",

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publisher = "Pharmaceutical Society of Japan",

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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

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