950849-05-5Relevant academic research and scientific papers
A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F
Oliver, Steven F.,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Smith, Martin D.,Ley, Steven V.
, p. 5996 - 6000 (2003)
An entirely substrate-controlled total synthesis of three members of the thapsigargin family (e.g. trilobolide) is achieved starting from (S)-carvone. The synthesis is linear in nature but is achieved in high yield (> 90% per step). The route permits late
Study towards diversity oriented synthesis of optically active substituted cyclopentane fused carbocyclic and oxacyclic medium-sized rings: Competition between Grubbs-II catalyzed ring closing olefin metathesis and ring closing carbonyl-olefin metathesis
Chakraborty,Roy
, p. 1831 - 1840 (2016/12/16)
A study towards diversity-oriented synthesis of optically active cyclopentane fused bicyclic frameworks has been accomplished. The common intermediate was prepared from commercially available starting material (S)-carvone. The observations on competition
Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition
Andrews, Stephen P.,Ball, Matthew,Wierschem, Frank,Cleator, Ed,Oliver, Steven,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Huenger, Udo,Smith, Martin D.,Ley, Steven V.
, p. 5688 - 5712 (2008/02/13)
Herein we describe the total synthesis of five guaianolide natural products: thapsigargin. thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for further investigation of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.
