Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

Tom D Ackrill; Hazel A Sparkes; Chris L Willis

doi:10.1021/acs.orglett.5b01848

Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

Tom D Ackrill, Hazel A Sparkes, Chris L Willis^*

^*Corresponding author for this work

School of Chemistry

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

22 Citations (Scopus)

428 Downloads (Pure)

Abstract

γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.

Original language	English
Pages (from-to)	3884-3887
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.5b01848
Publication status	Published - 7 Aug 2015

Bibliographical note

Date of Acceptance: 24/07/2015

Research Groups and Themes

Bristol BioDesign Institute
Organic & Biological

Keywords

synthetic biology

Access to Document

10.1021/acs.orglett.5b01848

Ackrill_Paper_2015_15
© 2015 American Chemical Society
Accepted author manuscript, 586 KBLicence: CC BY-NC

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title = "Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J",

abstract = "γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.",

keywords = "synthetic biology",

author = "Ackrill, \{Tom D\} and Sparkes, \{Hazel A\} and Willis, \{Chris L\}",

note = "Date of Acceptance: 24/07/2015",

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doi = "10.1021/acs.orglett.5b01848",

language = "English",

volume = "17",

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journal = "Organic Letters",

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T1 - Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

AU - Ackrill, Tom D

AU - Sparkes, Hazel A

AU - Willis, Chris L

N1 - Date of Acceptance: 24/07/2015

PY - 2015/8/7

Y1 - 2015/8/7

N2 - γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.

AB - γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.

KW - synthetic biology

UR - http://www.scopus.com/inward/record.url?scp=84938854640&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b01848

DO - 10.1021/acs.orglett.5b01848

M3 - Article (Academic Journal)

C2 - 26208000

AN - SCOPUS:84938854640

SN - 1523-7060

VL - 17

SP - 3884

EP - 3887

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

Abstract

Bibliographical note

Research Groups and Themes

Keywords

Access to Document

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A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

HIGH-FIELD NMR SPECTROSCOPY FOR BIOMOLECULAR RESEARCH

Cite this

Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

Abstract

Bibliographical note

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

HIGH-FIELD NMR SPECTROSCOPY FOR BIOMOLECULAR RESEARCH

Cite this