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

Pattarakiat Seankongsuk; Patcharaporn Sae-Lao; Shi He; Veronica Pereira; Roderick W. Bates

doi:10.1039/d5ob00162e

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

Pattarakiat Seankongsuk, Patcharaporn Sae-Lao, Shi He, Veronica Pereira, Roderick W. Bates^*

^*Corresponding author for this work

Nanyang Technological University

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

Abstract

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.

Original language	English
Journal	Organic and Biomolecular Chemistry
DOIs	https://doi.org/10.1039/d5ob00162e
Publication status	Accepted/In press - 2025
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2025 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d5ob00162e

Cite this

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title = "Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation",

abstract = "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.",

author = "Pattarakiat Seankongsuk and Patcharaporn Sae-Lao and Shi He and Veronica Pereira and Bates, {Roderick W.}",

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year = "2025",

doi = "10.1039/d5ob00162e",

language = "English",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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T1 - Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation

AU - Seankongsuk, Pattarakiat

AU - Sae-Lao, Patcharaporn

AU - He, Shi

AU - Pereira, Veronica

AU - Bates, Roderick W.

PY - 2025

Y1 - 2025

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AB - 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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DO - 10.1039/d5ob00162e

M3 - Article

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SN - 1477-0520

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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