Synthesis of sphingosine-related azetidine alkaloids, penaresidins: Construction of highly substituted azetidine rings

Tomoya Fujiwara; Takayuki Yakura

doi:10.3987/REV-19-SR(F)3

Synthesis of sphingosine-related azetidine alkaloids, penaresidins: Construction of highly substituted azetidine rings

Tomoya Fujiwara, Takayuki Yakura^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

3 Scopus citations

Abstract

Penaresidin A and B are sphingosine-related natural products that contain a 2,3,4-trisubstituted azetidine ring and a long alkyl side chain. Stereoselective construction of the trisubstituted azetidine ring is a crucial step in the synthesis of penaresidins, and all the currently reported syntheses have been accomplished by S_N2-type cyclization of a precursor having a 1-amino-2,3-diol structure with three continuous stereocenters. This cyclization is strongly influenced by the configurations of the vicinal amino alcohol moieties of the precursors. This review focuses on the S_N2-type cyclizations that are used to construct the trisubstituted azetidine ring in penaresidin synthesis.

Original language	English
Pages (from-to)	383-406
Number of pages	24
Journal	Heterocycles
Volume	101
Issue number	2
DOIs	https://doi.org/10.3987/REV-19-SR(F)3
State	Published - 2020

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Synthesis of sphingosine-related azetidine alkaloids, penaresidins: Construction of highly substituted azetidine rings",

abstract = "Penaresidin A and B are sphingosine-related natural products that contain a 2,3,4-trisubstituted azetidine ring and a long alkyl side chain. Stereoselective construction of the trisubstituted azetidine ring is a crucial step in the synthesis of penaresidins, and all the currently reported syntheses have been accomplished by SN2-type cyclization of a precursor having a 1-amino-2,3-diol structure with three continuous stereocenters. This cyclization is strongly influenced by the configurations of the vicinal amino alcohol moieties of the precursors. This review focuses on the SN2-type cyclizations that are used to construct the trisubstituted azetidine ring in penaresidin synthesis.",

author = "Tomoya Fujiwara and Takayuki Yakura",

note = "Publisher Copyright: {\textcopyright} 2020 The Japan Institute of Heterocyclic Chemistry.",

year = "2020",

doi = "10.3987/REV-19-SR(F)3",

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T1 - Synthesis of sphingosine-related azetidine alkaloids, penaresidins

T2 - Construction of highly substituted azetidine rings

AU - Fujiwara, Tomoya

AU - Yakura, Takayuki

PY - 2020

Y1 - 2020

N2 - Penaresidin A and B are sphingosine-related natural products that contain a 2,3,4-trisubstituted azetidine ring and a long alkyl side chain. Stereoselective construction of the trisubstituted azetidine ring is a crucial step in the synthesis of penaresidins, and all the currently reported syntheses have been accomplished by SN2-type cyclization of a precursor having a 1-amino-2,3-diol structure with three continuous stereocenters. This cyclization is strongly influenced by the configurations of the vicinal amino alcohol moieties of the precursors. This review focuses on the SN2-type cyclizations that are used to construct the trisubstituted azetidine ring in penaresidin synthesis.

AB - Penaresidin A and B are sphingosine-related natural products that contain a 2,3,4-trisubstituted azetidine ring and a long alkyl side chain. Stereoselective construction of the trisubstituted azetidine ring is a crucial step in the synthesis of penaresidins, and all the currently reported syntheses have been accomplished by SN2-type cyclization of a precursor having a 1-amino-2,3-diol structure with three continuous stereocenters. This cyclization is strongly influenced by the configurations of the vicinal amino alcohol moieties of the precursors. This review focuses on the SN2-type cyclizations that are used to construct the trisubstituted azetidine ring in penaresidin synthesis.

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Synthesis of sphingosine-related azetidine alkaloids, penaresidins: Construction of highly substituted azetidine rings

Abstract

ASJC Scopus subject areas

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