Synthetic and Biosynthetic Methods for Selective Cyclisations of 4,5-Epoxy Alcohols to Tetrahydropyrans

James I Bowen; Luoyi Wang; Matthew P Crump; Chris L Willis

doi:10.1039/D1OB01905H

Synthetic and Biosynthetic Methods for Selective Cyclisations of 4,5-Epoxy Alcohols to Tetrahydropyrans

James I Bowen, Luoyi Wang, Matthew P Crump, Chris L Willis^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

Tetrahydropyrans (THPs) are common structural motifs found in natural products and synthetic therapeutic molecules. In Nature these 6-membered oxygen heterocycles are often assembled via intramolecular reactions involving either oxy-Michael additions or ring opening of epoxy-alcohols. Indeed, the polyether natural products have been particularly widely studied due to their fascinating structures and important biological properties; these are commonly formed via endo-selective epoxide-opening cascades. In this review we outline synthetic approaches for endo-selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols and their applications in natural product synthesis. In addition, the biosynthesis of THP-containing natural products which utilise IERO reactions are reviewed.

Original language	English
Article number	20
Pages (from-to)	1150-1175
Number of pages	26
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	6
DOIs	https://doi.org/10.1039/D1OB01905H
Publication status	Published - 14 Jan 2022

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Publisher Copyright:
© The Royal Society of Chemistry.

Research Groups and Themes

BCS and TECS CDTs
BrisSynBio
Bristol BioDesign Institute
Organic & Biological

Keywords

synthetic biology

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title = "Synthetic and Biosynthetic Methods for Selective Cyclisations of 4,5-Epoxy Alcohols to Tetrahydropyrans",

abstract = "Tetrahydropyrans (THPs) are common structural motifs found in natural products and synthetic therapeutic molecules. In Nature these 6-membered oxygen heterocycles are often assembled via intramolecular reactions involving either oxy-Michael additions or ring opening of epoxy-alcohols. Indeed, the polyether natural products have been particularly widely studied due to their fascinating structures and important biological properties; these are commonly formed via endo-selective epoxide-opening cascades. In this review we outline synthetic approaches for endo-selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols and their applications in natural product synthesis. In addition, the biosynthesis of THP-containing natural products which utilise IERO reactions are reviewed.",

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AU - Bowen, James I

AU - Wang, Luoyi

AU - Crump, Matthew P

AU - Willis, Chris L

PY - 2022/1/14

Y1 - 2022/1/14

N2 - Tetrahydropyrans (THPs) are common structural motifs found in natural products and synthetic therapeutic molecules. In Nature these 6-membered oxygen heterocycles are often assembled via intramolecular reactions involving either oxy-Michael additions or ring opening of epoxy-alcohols. Indeed, the polyether natural products have been particularly widely studied due to their fascinating structures and important biological properties; these are commonly formed via endo-selective epoxide-opening cascades. In this review we outline synthetic approaches for endo-selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols and their applications in natural product synthesis. In addition, the biosynthesis of THP-containing natural products which utilise IERO reactions are reviewed.

AB - Tetrahydropyrans (THPs) are common structural motifs found in natural products and synthetic therapeutic molecules. In Nature these 6-membered oxygen heterocycles are often assembled via intramolecular reactions involving either oxy-Michael additions or ring opening of epoxy-alcohols. Indeed, the polyether natural products have been particularly widely studied due to their fascinating structures and important biological properties; these are commonly formed via endo-selective epoxide-opening cascades. In this review we outline synthetic approaches for endo-selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols and their applications in natural product synthesis. In addition, the biosynthesis of THP-containing natural products which utilise IERO reactions are reviewed.

KW - synthetic biology

U2 - 10.1039/D1OB01905H

DO - 10.1039/D1OB01905H

M3 - Article (Academic Journal)

SN - 1477-0520

VL - 20

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EP - 1175

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

M1 - 20

ER -

Synthetic and Biosynthetic Methods for Selective Cyclisations of 4,5-Epoxy Alcohols to Tetrahydropyrans

Abstract

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