123269-03-4Relevant 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 (2007)
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).
Concise synthesis of thapsigargin from nortrilobolide
Crestey, Fran?ois,Toma, Maddalena,Christensen, S?ren Br?gger
, p. 5896 - 5898 (2015)
Herein, we describe an expedient synthesis of the hexaoxygenated guaianolide thapsigargin (1), a potent inhibitor of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA), from the natural product nortrilobolide (2). This protocol involves three key steps: the one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, subsequent stereoselective α′-acyloxylation in the presence of Mn(OAc)3, and a highly stereoselective ketone reduction.
METHOD FOR PREPARATION OF INTERMEDIATES USEFUL FOR PREPARATION OF THAPSIGARGIN AND NORTRILOBOLIDE
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, (2018/09/25)
The present invention relates to the preparation of Thapsigargin (1) and Nortrilobolide (2). The invention further relates to intermediates and preparation of said intermediates which are useful for the preparation of (1) and (2).