Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxyerythrinans: total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine

Shinzo Hosoi; Motoyoshi Nagao; Yoshisuke Tsuda; Kimiaki Isobe; Takehiro Sano; Tomihisa Ohta

doi:10.1039/B001906M

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Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxyerythrinans: total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine¹

Shinzo Hosoi,*^a Motoyoshi Nagao,^a Yoshisuke Tsuda,^a Kimiaki Isobe,^b Takehiro Sano^b and Tomihisa Ohta^a

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* Corresponding authors

^a Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa, Japan

^b Showa Pharmaceutical University, Machida, Tokyo, Japan

Abstract

Four stereoisomers of 1,2-epoxy-3-hydroxyerythrinans are synthesized and their stereochemistries determined unambiguously. Of these, the 1,2α-epoxy-3α-alcohol 4 is converted to the alkenoid-type alkaloid, (±)-erythratidine 1, utilizing reductive migration of an α,β-unsaturated γ,δ-epoxyamide with samarium diiodide as a key step.

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Article information

DOI: https://doi.org/10.1039/B001906M
Article type: Paper
Submitted: 08 Mar 2000
Accepted: 04 Apr 2000
First published: 02 May 2000

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J. Chem. Soc., Perkin Trans. 1, 2000, 1505-1511

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Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxyerythrinans: total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine

S. Hosoi, M. Nagao, Y. Tsuda, K. Isobe, T. Sano and T. Ohta, J. Chem. Soc., Perkin Trans. 1, 2000, 1505 DOI: 10.1039/B001906M

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Journal of the Chemical Society, Perkin Transactions 1