Total synthesis of (+/-)-asteriscanolide.
The total synthesis of asteriscanolide (1) has been achieved by taking advantage on an intermolecular Pauson-Khand cycloaddition and a ring-closing metathesis as key bond-forming transformations. The approach incorporates the cyclooctane stereogenic center prior to ring formation. Interestingly, the ring-closing metathesis generates a new eight-membered ring with an "in-out" intrabridgehead relationship.
Krafft
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ME
Department of Chemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. mek@chem.fsu.edu
Cheung
Y Y
YY
Abboud
K A
KA
D003500:Cyclization; D034242:Cyclooctanes; D007659:Ketones / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis; D012717:Sesquiterpenes / Q000138:chemical synthesis*
D034242:Cyclooctanes; D007659:Ketones; D007783:Lactones; D012717:Sesquiterpenes; C449084:asteriscanolide; C044494:cyclooctanone