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

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › 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.

Original language	English
Pages (from-to)	7639-7642
Number of pages	4
Journal	Organic Letters
Volume	27
Issue number	28
DOIs	https://doi.org/10.1021/acs.orglett.5c02231
Publication status	Published - 18 Jul 2025

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10.1021/acs.orglett.5c02231

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title = "Mimicking Nature in Reshaping the Triterpene Skeleton: Synthesis of a Class of Unnatural Oleanane Derivatives",

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.",

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T2 - Synthesis of a Class of Unnatural Oleanane Derivatives

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

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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

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JO - Organic Letters

JF - Organic Letters

IS - 28

ER -

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

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