Selective synthesis of 13-epi-manoyl oxide

Morărescu (Chetraru) Olga; Traistari Marionela; Barba Alic; Duka Gh.; Ungur Nikon; Kulciţki Veaceslav

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2023-05-28 04:01

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547:577:576 (1)

Chimie organică (484)

Bazele materiale ale vieții. Biochimie. Biologie moleculară. Biofizică (664)

Biologie celulară și subcelulară. Citologie (130)

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MORĂRESCU (CHETRARU), Olga, TRAISTARI, Marionela, BARBA, Alic, DUKA, Gh., UNGUR, Nikon, KULCIŢKI, Veaceslav. Selective synthesis of 13-epi-manoyl oxide. In: New frontiers in natural product chemistry.: A destiny on the altar of research. Dedicated to academician Pavel Vlad, Ed. 6, 21 mai 2021, Chișinău. Chișinău, Republica Moldova: Tipografia "Artpoligraf", 2021, Ediția 6, p. 34. ISBN 978-9975-3336-7-2. DOI: https://doi.org/10.19261/nfnpc.2021.ab27

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New frontiers in natural product chemistry.
Ediția 6, 2021

Conferința " New frontiers in natural product chemistry."
6, Chișinău, Moldova, 21 mai 2021

Selective synthesis of 13-epi-manoyl oxide

DOI:https://doi.org/10.19261/nfnpc.2021.ab27

CZU: 547:577:576

Pag. 34-34

Morărescu (Chetraru) Olga¹, Traistari Marionela², Barba Alic¹, Duka Gh.¹, Ungur Nikon¹, Kulciţki Veaceslav¹

¹ Institute of Chemistry,
² Moldova State University

Proiecte:

Menționat în lucrare: 20.80009.5007.27 Mecanisme fizico-chimice a proceselor redox cu transfer de electroni implicate în sistemele vitale, tehnologice și de mediu

Disponibil în IBN: 28 mai 2021

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Labdane-type diterpenes are excellent examples of natural products with important pharmaceutical activities. Besides, several labdanes are quite abundant in nature and/or are commercially, such as sclareol 1. Hence, they are useful starting materials for chemical transformations. On the other hand, manoyl oxide 2 and 13-epi-manoyl oxide 3 are labdane compounds with skeleton identical to forskolin – a secondary metabolite isolated from Coleus forskohlii plant and showing a myriad of therapeutic activities [1], and other relevant natural compounds reported in structure-activity relationship (SAR) [2,3]. We have also demonstrated recently a free-radical procedure for structural modification of both forskolin and manoyl oxides [4,5] leading to an unusual distal functionalization of 13-epi- framework. In order to explore the full potential of such late-stage functionalization, one needs reliable sources of 13-epi-manoyl oxide 3, which ideally is made available via selective synthesis. The current work presents the selective one-step synthesis of 13-epi-manoyl oxide 3 basing on a low-temperature superacidic cyclization of sclareol 1 (Scheme 1). An older contribution of some of us reported an equimolar mixture of epimers [6]. Now, the reaction conditions have been finely tuned in order to achieve a 9:1 ratio in favor of the desired 13-epioxide 3. The preparative value of the elaborated procedure was convincingly demonstrated. Scheme 1

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