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Synthesis and biological evaluation of ( − )-13,14-dihydroxy-8,11,13-podocarpatrien-7-one and derivatives from (+)-manool

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journal contribution
posted on 20.12.2014 by María L. Novoa, Yelisbeth Escalante, Liliana Maldonado, Iván Galindo-Castro, Annamil Álvarez, Katherine Figarella, Sabrina Marsiccobetre, Irina Arocha, Jais Nieves, Franklin Salazar, Carlos Gámez, Nieves Canudas, Eleonora Tropper, Teresa González, José E. Villamizar

13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (1) and a series of ring C aromatic diterpene derivatives were synthesised from (+)-manool (4) and evaluated for their cytotoxic, leishmanicidal and trypanocidal activities. Our results indicated that compound 1 and other podocarpane-type intermediates are cytotoxic. Cleavage of C6–C7 bond of compound 7 improved cytotoxic activity, indicating that, in particular, the 6,7-seco-podocarpane-type compound 20 might serve as a lead compound for further development.