Structural Diversity from the Transannular Cyclizations of Natural Germacrone and Epoxy Derivatives: A Theoretical–Experimental Study |
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| Authors: | M Carmen Pérez Morales Dr Julieta V Catalán Dr Victoriano Domingo Prof Martín Jaraíz Dr M Mar Herrador Dr José F Quílez del Moral Prof José‐Luis López‐Pérez Prof Alejandro F Barrero |
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| Institution: | 1. Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuente Nueva, s/n, 18071 Granada (Spain), Fax: (+34)?958243318;2. Department of Electronics, ETSIT, University of Valladolid, Paseo de Belén 15, 47011 Valladolid (Spain);3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Salamanca, Avda. Campo Charro, s/n, 37007 Salamanca (Spain) |
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| Abstract: | Treatment of germacrone ( 1 ) with different electrophiles, and of its epoxy derivatives germacrone‐4,5‐epoxide ( 2 ), germacrone‐1,10‐epoxide ( 3 ) and isogermacrone‐4,5‐epoxide ( 4 ) with Brönsted/Lewis acids and TiIII, gives rise to a great structural diversity. Thus, by using a maximum of two steps, the production of more than 40 compounds corresponding to 14 skeletons is described. Computational calculations rationalizing the structural divergence produced are also described. Finally, since some of the compounds generated are bioactive natural sesquiterpenes, the mechanisms of formation of these substances will provide new insights in their biosynthesis. |
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| Keywords: | biosynthesis conformational analysis density functional calculations ring closure terpenes |
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