Selective synthesis of 13-epi-manoyl oxide
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MORĂRESCU (CHETRARU), Olga; TRAISTARI, Marionela; BARBA, Alic; DUCA, Gheorghe; UNGUR, Nicon; 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. Ediția 6, 4 iunie 2021, Chișinău. Chișinău: Institute of Chemistry, 2021, p. 34.
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New frontiers in natural product chemistry.
Ediția 6, 2021
Seminarul " New frontiers in natural product chemistry."
Chișinău, Moldova, 4 iunie 2021

Selective synthesis of 13-epi-manoyl oxide


DOI: 10.19261/nfnpc.2021.ab27
CZU: 547:577:576
Pag. 34-34

Morărescu (Chetraru) Olga1, Traistari Marionela2, Barba Alic1, Duca Gheorghe1, Ungur Nicon1, Kulciţki Veaceslav1
 
1 Institute of Chemistry,
2 State University of Moldova
 
Proiect:
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


Rezumat

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