A concise synthesis of anti-bicyclo[6.1.0]nonyne carboxylic acid

Mackenzie Weir; Beatrice Vaccari; Aidan Matthews; Graeme Turnbull; Valery Kozhevnikov

doi:10.1039/D4RA06708H

A concise synthesis of anti-bicyclo[6.1.0]nonyne carboxylic acid

Mackenzie Weir, Beatrice Vaccari, Aidan Matthews, Graeme Turnbull, Valery Kozhevnikov^*

^*Corresponding author for this work

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

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Abstract

Bicyclo[6.1.0]nonyne carboxylic acid (BCN-COOH) is a valuable intermediate for the development of bioorthogonal click reagents. A convenient three-step synthesis of pure diastereomer anti-BCN-COOH is reported here, with an overall yield of 32% starting from 1,5-cyclooctadiene. To the best of our knowledge, this is the shortest route to anti-BCN-COOH known to date. The new method compares favourably with the optimised four-step synthesis based on previously reported data.

Original language	English
Pages (from-to)	37400-37403
Number of pages	4
Journal	RSC Advances
Volume	14
Issue number	50
Early online date	21 Nov 2024
DOIs	https://doi.org/10.1039/D4RA06708H
Publication status	Published - 21 Nov 2024

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manuscript BCN-COOH_v3_revised_cleanAccepted author manuscript, 274 KBLicence: CC BY
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abstract = "Bicyclo[6.1.0]nonyne carboxylic acid (BCN-COOH) is a valuable intermediate for the development of bioorthogonal click reagents. A convenient three-step synthesis of pure diastereomer anti-BCN-COOH is reported here, with an overall yield of 32% starting from 1,5-cyclooctadiene. To the best of our knowledge, this is the shortest route to anti-BCN-COOH known to date. The new method compares favourably with the optimised four-step synthesis based on previously reported data.",

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AU - Weir, Mackenzie

AU - Vaccari, Beatrice

AU - Matthews, Aidan

AU - Turnbull, Graeme

AU - Kozhevnikov, Valery

PY - 2024/11/21

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N2 - Bicyclo[6.1.0]nonyne carboxylic acid (BCN-COOH) is a valuable intermediate for the development of bioorthogonal click reagents. A convenient three-step synthesis of pure diastereomer anti-BCN-COOH is reported here, with an overall yield of 32% starting from 1,5-cyclooctadiene. To the best of our knowledge, this is the shortest route to anti-BCN-COOH known to date. The new method compares favourably with the optimised four-step synthesis based on previously reported data.

AB - Bicyclo[6.1.0]nonyne carboxylic acid (BCN-COOH) is a valuable intermediate for the development of bioorthogonal click reagents. A convenient three-step synthesis of pure diastereomer anti-BCN-COOH is reported here, with an overall yield of 32% starting from 1,5-cyclooctadiene. To the best of our knowledge, this is the shortest route to anti-BCN-COOH known to date. The new method compares favourably with the optimised four-step synthesis based on previously reported data.

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JO - RSC Advances

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IS - 50

ER -

A concise synthesis of anti-bicyclo[6.1.0]nonyne carboxylic acid

Abstract

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