Toward the total synthesis of variecolin.
[reaction: see text] An annulative approach toward the total synthesis of the sesterterpenoid variecolin (1) is presented. Synthesis of the key hemiketal, containing the core ABC ring skeleton, has been achieved on a model system by an expeditious route utilizing samarium(II) iodide. Furthermore, enantioselective syntheses of component fragments for the total synthesis have been developed.
Molander
G A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Quirmbach
M S
MS
Silva
L F
LF
Spencer
K C
KC
Balsells
J
J
D057911:Angiotensin Receptor Antagonists; D007166:Immunosuppressive Agents / Q000138:chemical synthesis; D044140:Receptor, Angiotensin, Type 1; D044139:Receptor, Angiotensin, Type 2; D054830:Sesterterpenes; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
D057911:Angiotensin Receptor Antagonists; D007166:Immunosuppressive Agents; D044140:Receptor, Angiotensin, Type 1; D044139:Receptor, Angiotensin, Type 2; D054830:Sesterterpenes; D013729:Terpenes; C433945:variecolin