Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-Agelastatin A and (-)-Agelastatin B

Ken S. Feldman, Joe C. Saunders

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

The asymmetric total syntheses of (-)-agelastatin A and (-)-agelastatin B were accomplished in 14 steps each from (R)-epichlorohydrin. The pivotal transformation in both sequences was a sulfinate-promoted cyclization of an alkynyliodonium salt to furnish a key functionalized cyclopentene intermediate. Selective bromination in the final step led to either agelastatin A or agelastatin B, depending upon conditions.

Original languageEnglish (US)
Pages (from-to)9060-9061
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number31
DOIs
StatePublished - Aug 7 2002

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Synthetic Chemistry Techniques
Cyclization
Salts
Epichlorohydrin
Cyclopentanes
Halogenation
agelastatin A
agelastatin B

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-Agelastatin A and (-)-Agelastatin B. / Feldman, Ken S.; Saunders, Joe C.

In: Journal of the American Chemical Society, Vol. 124, No. 31, 07.08.2002, p. 9060-9061.

Research output: Contribution to journalArticle

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