Exploring Convergent Two-Step Synthetic Approaches to the Pancratistatin Framework

Gemma A. Di Iulio; Mary F. Mahon; Lorenzo Caggiano

doi:10.1002/slct.202202703

Exploring Convergent Two-Step Synthetic Approaches to the Pancratistatin Framework

Gemma A. Di Iulio, Mary F. Mahon, Lorenzo Caggiano

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

1 Citation (SciVal)

Abstract

Pancratistatin and narciclasine are natural products that display potent and selective antiproliferative activity against various cancer cells. We explore convergent synthetic routes to access the pancratistatin framework in just two steps, without the need for metal catalysis or activated substrates via a common indanone intermediate. The indanone is synthesised by intermolecular Friedel-Crafts acylation with trifluoroacetic acid anhydride (TFAA), by two alternative routes, and then undergoes a Schmidt reaction with TFA to generate the pancratistatin core. This concise approach offers the possibility of generating various pancratistatin analogues for further development.

Original language	English
Article number	e202202703
Journal	ChemistrySelect
Volume	7
Issue number	31
Early online date	18 Aug 2022
DOIs	https://doi.org/10.1002/slct.202202703
Publication status	Published - 19 Aug 2022

Bibliographical note

Funding Information:
We wish to thank Dr Timothy J. Woodman and Dr Anneke Lubben (University of Bath) for their assistance with the NMR and mass spectra, respectively. We are grateful to the University of Bath for providing a studentship for GAD.

Keywords

Acylation
Aromatic substitution
Brønsted acid catalysis
Nitrogen heterocycles
Synthetic methods

ASJC Scopus subject areas

General Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1002/slct.202202703Licence: CC BY

Cite this

@article{969366dde1214f838454a49e17dcebae,

title = "Exploring Convergent Two-Step Synthetic Approaches to the Pancratistatin Framework",

abstract = "Pancratistatin and narciclasine are natural products that display potent and selective antiproliferative activity against various cancer cells. We explore convergent synthetic routes to access the pancratistatin framework in just two steps, without the need for metal catalysis or activated substrates via a common indanone intermediate. The indanone is synthesised by intermolecular Friedel-Crafts acylation with trifluoroacetic acid anhydride (TFAA), by two alternative routes, and then undergoes a Schmidt reaction with TFA to generate the pancratistatin core. This concise approach offers the possibility of generating various pancratistatin analogues for further development.",

keywords = "Acylation, Aromatic substitution, Br{\o}nsted acid catalysis, Nitrogen heterocycles, Synthetic methods",

author = "{Di Iulio}, {Gemma A.} and Mahon, {Mary F.} and Lorenzo Caggiano",

note = "Funding Information: We wish to thank Dr Timothy J. Woodman and Dr Anneke Lubben (University of Bath) for their assistance with the NMR and mass spectra, respectively. We are grateful to the University of Bath for providing a studentship for GAD. ",

year = "2022",

month = aug,

day = "19",

doi = "10.1002/slct.202202703",

language = "English",

volume = "7",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley",

number = "31",

}

TY - JOUR

T1 - Exploring Convergent Two-Step Synthetic Approaches to the Pancratistatin Framework

AU - Di Iulio, Gemma A.

AU - Mahon, Mary F.

AU - Caggiano, Lorenzo

N1 - Funding Information: We wish to thank Dr Timothy J. Woodman and Dr Anneke Lubben (University of Bath) for their assistance with the NMR and mass spectra, respectively. We are grateful to the University of Bath for providing a studentship for GAD.

PY - 2022/8/19

Y1 - 2022/8/19

N2 - Pancratistatin and narciclasine are natural products that display potent and selective antiproliferative activity against various cancer cells. We explore convergent synthetic routes to access the pancratistatin framework in just two steps, without the need for metal catalysis or activated substrates via a common indanone intermediate. The indanone is synthesised by intermolecular Friedel-Crafts acylation with trifluoroacetic acid anhydride (TFAA), by two alternative routes, and then undergoes a Schmidt reaction with TFA to generate the pancratistatin core. This concise approach offers the possibility of generating various pancratistatin analogues for further development.

AB - Pancratistatin and narciclasine are natural products that display potent and selective antiproliferative activity against various cancer cells. We explore convergent synthetic routes to access the pancratistatin framework in just two steps, without the need for metal catalysis or activated substrates via a common indanone intermediate. The indanone is synthesised by intermolecular Friedel-Crafts acylation with trifluoroacetic acid anhydride (TFAA), by two alternative routes, and then undergoes a Schmidt reaction with TFA to generate the pancratistatin core. This concise approach offers the possibility of generating various pancratistatin analogues for further development.

KW - Acylation

KW - Aromatic substitution

KW - Brønsted acid catalysis

KW - Nitrogen heterocycles

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85136518912&partnerID=8YFLogxK

U2 - 10.1002/slct.202202703

DO - 10.1002/slct.202202703

M3 - Article

AN - SCOPUS:85136518912

SN - 2365-6549

VL - 7

JO - ChemistrySelect

JF - ChemistrySelect

IS - 31

M1 - e202202703

ER -

Exploring Convergent Two-Step Synthetic Approaches to the Pancratistatin Framework

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this