Mimicking Nature in Reshaping the Triterpene Skeleton: Synthesis of a Class of Unnatural Oleanane Derivatives

Edoardo di Biase; Ernesto Gargiulo; Daniela Imperio; Giuseppina Chianese; Diego Caprioglio; Hawraz Ibrahim M. Amin; Orazio Taglialatela-Scafati; Alberto Minassi

doi:10.1021/acs.orglett.5c02231

Mimicking Nature in Reshaping the Triterpene Skeleton: Synthesis of a Class of Unnatural Oleanane Derivatives

Edoardo di Biase
, Ernesto Gargiulo
, Daniela Imperio
, Giuseppina Chianese
, Diego Caprioglio
, Hawraz Ibrahim M. Amin
, Orazio Taglialatela-Scafati
, Alberto Minassi

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

The possibility of duplicating the efficiency and selectivity of natural processes under laboratory conditions remains a significant challenge for organic chemists. In this letter, we demonstrated that it is possible to introduce pinpoint modifications and to reshape the terpene skeleton of easily available oleananes in a biomimetic fashion. Furthermore, aromatization of the A ring of the triterpene system is reported here for the first time, mimicking what occurs exclusively in nature in sediments.

Lingua originale	Inglese
pagine (da-a)	7639-7642
Numero di pagine	4
Rivista	Organic Letters
Volume	27
Numero di pubblicazione	28
DOI	https://doi.org/10.1021/acs.orglett.5c02231
Stato di pubblicazione	Pubblicato - 18 lug 2025

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10.1021/acs.orglett.5c02231

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abstract = "The possibility of duplicating the efficiency and selectivity of natural processes under laboratory conditions remains a significant challenge for organic chemists. In this letter, we demonstrated that it is possible to introduce pinpoint modifications and to reshape the terpene skeleton of easily available oleananes in a biomimetic fashion. Furthermore, aromatization of the A ring of the triterpene system is reported here for the first time, mimicking what occurs exclusively in nature in sediments.",

author = "\{di Biase\}, Edoardo and Ernesto Gargiulo and Daniela Imperio and Giuseppina Chianese and Diego Caprioglio and Amin, \{Hawraz Ibrahim M.\} and Orazio Taglialatela-Scafati and Alberto Minassi",

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AU - di Biase, Edoardo

AU - Gargiulo, Ernesto

AU - Imperio, Daniela

AU - Chianese, Giuseppina

AU - Caprioglio, Diego

AU - Amin, Hawraz Ibrahim M.

AU - Taglialatela-Scafati, Orazio

AU - Minassi, Alberto

PY - 2025/7/18

Y1 - 2025/7/18

N2 - The possibility of duplicating the efficiency and selectivity of natural processes under laboratory conditions remains a significant challenge for organic chemists. In this letter, we demonstrated that it is possible to introduce pinpoint modifications and to reshape the terpene skeleton of easily available oleananes in a biomimetic fashion. Furthermore, aromatization of the A ring of the triterpene system is reported here for the first time, mimicking what occurs exclusively in nature in sediments.

AB - The possibility of duplicating the efficiency and selectivity of natural processes under laboratory conditions remains a significant challenge for organic chemists. In this letter, we demonstrated that it is possible to introduce pinpoint modifications and to reshape the terpene skeleton of easily available oleananes in a biomimetic fashion. Furthermore, aromatization of the A ring of the triterpene system is reported here for the first time, mimicking what occurs exclusively in nature in sediments.

UR - https://www.scopus.com/pages/publications/105010206722

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DO - 10.1021/acs.orglett.5c02231

M3 - Article

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JO - Organic Letters

JF - Organic Letters

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ER -

Mimicking Nature in Reshaping the Triterpene Skeleton: Synthesis of a Class of Unnatural Oleanane Derivatives

Abstract

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