Short and scalable synthesis of cynandione A

Short and scalable synthesis of cynandione A

A two-step gram-scale synthesis of cynandione A is described. The key to success is the one-pot tandem oxidation/regioselective arylation of 1,4-hydroquinone in the presence of an excess amount of oxidant. Natural bond orbital charge analysis was performed in order to understand the regioselectivity...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-03, Vol.21 (9), p.1868-1871
Hauptverfasser: Kang, Seoungwoo, Kim, Yeonjoon, Kim, Seonah, Ko, Ju Young, Kim, Jae Hyun
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Sprache:eng
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Animal models
Hydroquinone
Oxidants
Oxidation
Oxidizing agents
Regioselectivity
Synthesis
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container_end_page 1871
container_issue 9
container_start_page 1868
container_title Organic & biomolecular chemistry
container_volume 21
creator Kang, Seoungwoo
Kim, Yeonjoon
Kim, Seonah
Ko, Ju Young
Kim, Jae Hyun
description A two-step gram-scale synthesis of cynandione A is described. The key to success is the one-pot tandem oxidation/regioselective arylation of 1,4-hydroquinone in the presence of an excess amount of oxidant. Natural bond orbital charge analysis was performed in order to understand the regioselectivity of the arylation step. The highly practical and scalable synthesis developed herein is expected to assist the in-depth biological evaluation of cynandione A in various animal models. Two-step gram-scale synthesis of cynandione A was accomplished via one-pot tandem oxidation/regioselective arylation of 1,4-hydroquinone.
doi_str_mv 10.1039/d2ob02317b
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Animal models
Hydroquinone
Oxidants
Oxidation
Oxidizing agents
Regioselectivity
Synthesis
title Short and scalable synthesis of cynandione A
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