Asymmetric Synthesis\nof Taiwaniaquinone H via a Late-Stage\nOxidative Decarboxylation

The asymmetric syntheses of naturally occurring biologically\nrelevant <i>abeo</i>-abietane diterpenoids, (−)-taiwaniaquinone\nG\n(<b>1a</b>), and H (<b>1b</b>) have been reported via\na chiral pool strategy starting from commercially available abietic\nacid. A ring contraction of the middle ring of the [6,6,6]-carbotricyclic\nabietane diterpenoid core was carried out under the Wolff rearrangement.\nFinally, the synthesis of (−)-taiwaniaquinone H (<b>1b</b>) was completed via a one-pot CAN-mediated oxidative decarboxylation.

Publication Details

Journal
Figshare
Published
2024-11-22
DOI
https://doi.org/10.1021/acs.joc.4c02448.s001
Primary Topic
Biological Activity of Diterpenoids and Biflavonoids
Type
article
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article

Asymmetric Synthesis\nof Taiwaniaquinone H via a Late-Stage\nOxidative Decarboxylation

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Biological Activity of Diterpenoids and Biflavonoids
article

Asymmetric Synthesis\nof Taiwaniaquinone H via a Late-Stage\nOxidative Decarboxylation

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Abstract

The asymmetric syntheses of naturally occurring biologically\nrelevant <i>abeo</i>-abietane diterpenoids, (−)-taiwaniaquinone\nG\n(<b>1a</b>), and H (<b>1b</b>) have been reported via\na chiral pool strategy starting from commercially available abietic\nacid. A ring contraction of the middle ring of the [6,6,6]-carbotricyclic\nabietane diterpenoid core was carried out under the Wolff rearrangement.\nFinally, the synthesis of (−)-taiwaniaquinone H (<b>1b</b>) was completed via a one-pot CAN-mediated oxidative decarboxylation.

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Biological Activity of Diterpenoids and Biflavonoids
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Asymmetric Synthesis\nof Taiwaniaquinone H via a Late-Stage\nOxidative Decarboxylation · Figshare (2024) | TGRS Research Map | TGRS