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The guaianolide ring containing sesquiterpene thapsigargin is found in the roots and fruits of Mediterranean plant Thapsia garganica L. It is known for its activity as a potent antagonist for Ca2+-ATPase (sarco–endoplasmic reticulum Ca2+-ATPase) inhibition. Recently, a prodrug mipsagargin is being investigated to target the blood vessel of the cancer cells for the treatment of tumors. The limited natural supply (low isolation and only localized growth (Mediterranean area)) from the natural sources strongly urges for the development of chemical synthetic strategies to access these natural products. This review pertain the various strategies used so far in the thapsigargin’s synthesis, focusing on major contributions in the total synthesis till date. 相似文献
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Andrews SP Ball M Wierschem F Cleator E Oliver S Högenauer K Simic O Antonello A Hünger U Smith MD Ley SV 《Chemistry (Weinheim an der Bergstrasse, Germany)》2007,13(20):5688-5712
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. 相似文献
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