Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A
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Torres, Alejandro; Gutierrez, Pilar; Alvarez-Manzaneda Roldán, Ramón Jesús; Chahboun, Rachid; Alvarez-Manzaneda, EnriqueDate
2016-09-20Abstract
The first syntheses of cytotoxic marine arenarans A and B starting from commercial (−)-sclareol are reported. The oxocene ring of the target compound is formed via ring-closing metathesis, a process that depends on certain structural requirements. The trans-fused structure of the natural product is confirmed by comparison with the cis-fused isomer, which was synthesized. This synthetic strategy is also applicable to the synthesis of other oxocene terpenes.