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Total Synthesis of Five Thapsigargins: Guaianolide Natural Products Exhibiting Sub‐Nanomolar SERCA Inhibition
Author(s) -
Andrews Stephen P.,
Ball Matthew,
Wierschem Frank,
Cleator Ed,
Oliver Steven,
Högenauer Klemens,
Simic Oliver,
Antonello Alessandra,
Hünger Udo,
Smith Martin D.,
Ley Steven V.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700302
Subject(s) - thapsigargin , total synthesis , chemistry , in vivo , prodrug , serca , cytotoxicity , stereochemistry , in vitro , biochemistry , biology , enzyme , endoplasmic reticulum , microbiology and biotechnology , atpase
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.