930280-05-0Relevant articles and documents
Total synthesis of thapsigargin, a potent SERCA pump inhibitor
Ball, Matthew,Andrews, Stephen P.,Wierschem, Frank,Cleator, Ed,Smith, Martin D.,Ley, Steven V.
, p. 663 - 666 (2008/02/05)
The enantioselective total synthesis of thapsigargin, a potent, selective inhibitor of the Ca2+ pump SERCA, is described. Starting from ketoalcohol 8, key steps involve regioselective introduction of the internal olefin at C4-C5, judicious protecting group choice to allow chelation-controlled reduction at C3, and chemoselective introduction of the angelate ester function at C3-0. A selective esterification approach completes the total synthesis in a total of 42 steps and 0.61% overall yield (88.6% average yield per step).
