Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation

The first asymmetric synthesis of (−)-dihydrogambirtannine has been achieved using nucleophilic addition to a chiral sulfinyl imine to establish the stereogenic centre and [2 + 2 + 2] alkyne cyclotrimerisation to construct the aromatic E ring.

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Main Authors: Seankongsuk, Pattarakiat, Sae-Lao, Patcharaporn, He, Shi, Pereira, Veronica, Bates, Roderick W.
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2025
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Online Access:https://hdl.handle.net/10356/182986
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1829862025-03-14T15:32:09Z Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation Seankongsuk, Pattarakiat Sae-Lao, Patcharaporn He, Shi Pereira, Veronica Bates, Roderick W. School of Chemistry, Chemical Engineering and Biotechnology Chemistry The first asymmetric synthesis of (−)-dihydrogambirtannine has been achieved using nucleophilic addition to a chiral sulfinyl imine to establish the stereogenic centre and [2 + 2 + 2] alkyne cyclotrimerisation to construct the aromatic E ring. National Research Foundation (NRF) Published version We thank the National Research Foundation, Singapore, NRF Competitive Research Programme (CRP), grant numbers NRF-CRP27-2021-0002 and NRF-CRP18-2017-01, for financial support. We thank NTU for support. V. P. thanks the URECA programme of NTU. 2025-03-13T08:14:20Z 2025-03-13T08:14:20Z 2025 Journal Article Seankongsuk, P., Sae-Lao, P., He, S., Pereira, V. & Bates, R. W. (2025). Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation. Organic & Biomolecular Chemistry. https://dx.doi.org/10.1039/D5OB00162E 1477-0539 https://hdl.handle.net/10356/182986 10.1039/D5OB00162E en NRF-CRP27-2021-0002 NRF-CRP18-2017-01 Organic & Biomolecular Chemistry © The Royal Society of Chemistry 2025. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Chemistry
spellingShingle Chemistry
Seankongsuk, Pattarakiat
Sae-Lao, Patcharaporn
He, Shi
Pereira, Veronica
Bates, Roderick W.
Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation
description The first asymmetric synthesis of (−)-dihydrogambirtannine has been achieved using nucleophilic addition to a chiral sulfinyl imine to establish the stereogenic centre and [2 + 2 + 2] alkyne cyclotrimerisation to construct the aromatic E ring.
author2 School of Chemistry, Chemical Engineering and Biotechnology
author_facet School of Chemistry, Chemical Engineering and Biotechnology
Seankongsuk, Pattarakiat
Sae-Lao, Patcharaporn
He, Shi
Pereira, Veronica
Bates, Roderick W.
format Article
author Seankongsuk, Pattarakiat
Sae-Lao, Patcharaporn
He, Shi
Pereira, Veronica
Bates, Roderick W.
author_sort Seankongsuk, Pattarakiat
title Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation
title_short Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation
title_full Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation
title_fullStr Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation
title_full_unstemmed Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation
title_sort synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation
publishDate 2025
url https://hdl.handle.net/10356/182986
_version_ 1827070707077480448