Non-natural Elemane as the “Stepping Stone” for the Synthesis of Germacrane and Guaiane Sesquiterpenes Elissavet E. Anagnostaki Alexandros L. Zografos 10.1021/ol3031999.s001 https://acs.figshare.com/articles/journal_contribution/Non_natural_Elemane_as_the_Stepping_Stone_for_the_Synthesis_of_Germacrane_and_Guaiane_Sesquiterpenes/2455552 The synthesis of hydroxyelemane <b>5</b> from (<i>R</i>)-carvone and its utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction to access the 10-membered macrocyclic core of germacranes and the condensed 5–7 carbocycles of guaiane sesquiterpenes. Additionally, reactions of furanoguaianes under acidic or oxidizing reagents have been investigated, and preliminary results of these conversions are presented. 2013-01-04 00:00:00 furanoguaiane stereoselective tandem conversion utilization scaffold enantio access carbocycle core Guaiane SesquiterpenesThe synthesis guaiane sesquiterpenes oxidizing reagent Germacrane acidic Elemane hydroxyelemane macrocyclic germacrane Stepping rearrangement membered Synthesi biomimetic