Stereocontrolled synthesis of the aconitine D ring from d-glucose

Ian A. Pocock; Julien Doulcet; Craig R. Rice; Joseph B. Sweeney; Duncan M. Gill

doi:10.1039/d4ob00561a

Stereocontrolled synthesis of the aconitine D ring from d-glucose

Ian A. Pocock, Julien Doulcet, Craig R. Rice, Joseph B. Sweeney, Duncan M. Gill

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

2 Citations (Scopus)

Abstract

The synthesis of a fully oxygenated aconitine D ring precursor from (d)-(+)-glucose is described. The route features a highly diastereoselective alkynyl Grignard ketone addition and a base-mediated enelactone to 1,3-diketone rearrangement.

Original language	English
Pages (from-to)	4347-4352
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	22
Issue number	21
Early online date	3 May 2024
DOIs	https://doi.org/10.1039/d4ob00561a
Publication status	Published - 7 Jun 2024

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10.1039/d4ob00561aLicence: CC BY

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title = "Stereocontrolled synthesis of the aconitine D ring from d-glucose",

abstract = "The synthesis of a fully oxygenated aconitine D ring precursor from (d)-(+)-glucose is described. The route features a highly diastereoselective alkynyl Grignard ketone addition and a base-mediated enelactone to 1,3-diketone rearrangement.",

keywords = "Glucose, Ketones, Aconitine",

author = "Pocock, \{Ian A.\} and Julien Doulcet and Rice, \{Craig R.\} and Sweeney, \{Joseph B.\} and Gill, \{Duncan M.\}",

note = "Funding Information: The authors thank the Leverhulme Trust (Research Grant RPG-2014-115) and the University of Huddersfield for support of this project. Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

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T1 - Stereocontrolled synthesis of the aconitine D ring from d-glucose

AU - Pocock, Ian A.

AU - Doulcet, Julien

AU - Rice, Craig R.

AU - Sweeney, Joseph B.

AU - Gill, Duncan M.

N1 - Funding Information: The authors thank the Leverhulme Trust (Research Grant RPG-2014-115) and the University of Huddersfield for support of this project. Publisher Copyright: © 2024 The Royal Society of Chemistry.

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Y1 - 2024/6/7

N2 - The synthesis of a fully oxygenated aconitine D ring precursor from (d)-(+)-glucose is described. The route features a highly diastereoselective alkynyl Grignard ketone addition and a base-mediated enelactone to 1,3-diketone rearrangement.

AB - The synthesis of a fully oxygenated aconitine D ring precursor from (d)-(+)-glucose is described. The route features a highly diastereoselective alkynyl Grignard ketone addition and a base-mediated enelactone to 1,3-diketone rearrangement.

KW - Glucose

KW - Ketones

KW - Aconitine

UR - https://www.scopus.com/pages/publications/85192797482

U2 - 10.1039/d4ob00561a

DO - 10.1039/d4ob00561a

M3 - Article

AN - SCOPUS:85192797482

SN - 1477-0520

VL - 22

SP - 4347

EP - 4352

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 21

ER -

Stereocontrolled synthesis of the aconitine D ring from d-glucose

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