Phosphate tethers in natural product synthesis

Paul R. Hanson, Susanthi Jayasinghe, Soma Maitra, Jana L. Markley

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Recent advances in phosphate tether-mediated natural product synthesis are reviewed. Synthetic approaches toward dolabelide C, (–)-salicylihalimide A, (–)-tetrahydrolipstatin, and (+)-strictifolione are included. In addition, current efforts in method development are briefly reviewed, including a detailed study on the effect of stereochemical complexity on the phosphate-mediated, diastereoselective ring-closing metathesis reaction and recent advances in multi-reaction, one-pot sequential processes mediated by the phosphate tether. Overall, this review seeks to highlight the utility of phosphate triesters to serve as multifunctional tethers with protecting group and latent leaving group characteristics and the ability to orchestrate multiple, orthogonal reaction pathways to allow for the facile synthesis of complex, bioactive small molecules and their analogs.

Original languageEnglish (US)
Pages (from-to)253-272
Number of pages20
JournalTopics in Current Chemistry
Volume361
DOIs
StatePublished - 2014
Externally publishedYes

Bibliographical note

Funding Information:
The authors would like to thank the National Institute of General Medical Sciences (NIH R01 GM077309) and the State of Kansas for their generous support of our program.

Publisher Copyright:
© Springer International Publishing Switzerland 2015.

Keywords

  • Chemical methods
  • Chemoselective transformations
  • Cross metathesis (CM)
  • Natural product synthesis
  • One-pot
  • Phosphate
  • Phosphorus-based tether systems
  • Ring-closing metathesis (RCM)
  • Sequential processes
  • Tether methodologies

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