Total syntheses of secalonic acids A and D

Tian Qin, John A. Porco

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Total syntheses of the dimeric tetrahydroxanthone natural products secalonic acids A and D are described. Key steps involve kinetic resolution of the tetrahydroxanthone core structure using homobenzotetramisole catalysis and late-stage copper(I)-mediated homodimerization of complex aryl stannane monomers. It takes two: Concise syntheses of the natural products secalonic acids A and D using copper(I)-mediated dimerization of complex aryl stannane monomers to construct the requisite 2,2′-biphenol linkage are reported. Highly efficient kinetic resolution of the monomeric tetrahydroxanthone core structures was achieved using homobenzotetramisole catalysis. DMA=N,N-dimethyl acetamide, MOM=methoxymethyl.

Original languageEnglish (US)
Pages (from-to)3107-3110
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number12
DOIs
StatePublished - Mar 17 2014
Externally publishedYes

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Biological Products
Catalysis
Copper
Monomers
Kinetics
Dimerization
Acids
Dynamic mechanical analysis
secalonic acid
stannane
acetamide

Keywords

  • dimerization
  • kinetic resolution
  • natural products
  • stannanes
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Total syntheses of secalonic acids A and D. / Qin, Tian; Porco, John A.

In: Angewandte Chemie - International Edition, Vol. 53, No. 12, 17.03.2014, p. 3107-3110.

Research output: Contribution to journalArticle

Qin, Tian ; Porco, John A. / Total syntheses of secalonic acids A and D. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 12. pp. 3107-3110.
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