Total synthesis of thapsigargin, a potent SERCA pump inhibitor

Org Lett. 2007 Feb 15;9(4):663-6. doi: 10.1021/ol062947x. Epub 2007 Jan 27.

Abstract

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-O. 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). [reaction: see text].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Alkenes / chemistry
  • Chelating Agents / chemistry
  • Enzyme Inhibitors / chemical synthesis*
  • Indicators and Reagents
  • Oxidation-Reduction
  • Sarcoplasmic Reticulum Calcium-Transporting ATPases / antagonists & inhibitors*
  • Stereoisomerism
  • Thapsigargin / chemical synthesis*

Substances

  • Alcohols
  • Alkenes
  • Chelating Agents
  • Enzyme Inhibitors
  • Indicators and Reagents
  • Thapsigargin
  • Sarcoplasmic Reticulum Calcium-Transporting ATPases