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