Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling

Xiaowei Wu, Takayuki Iwata, Adam Scharf, Tian Qin, Kyle D. Reichl, John A. Porco

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The first synthesis of the chromanone lactone dimer gonytolide A has been achieved employing vanadium(V)-mediated oxidative coupling of the monomer gonytolide C. An o-bromine blocking group strategy was employed to favor para-para coupling and to enable kinetic resolution of (±)-gonytolide C. Asymmetric conjugate reduction enabled practical kinetic resolution of a chiral, racemic precursor and the asymmetric synthesis of (+)-gonytolide A and its atropisomer.

Original languageEnglish (US)
Pages (from-to)5969-5975
Number of pages7
JournalJournal of the American Chemical Society
Volume140
Issue number18
DOIs
StatePublished - May 9 2018
Externally publishedYes

Fingerprint

Oxidative Coupling
Bromine
Vanadium
Kinetics
Lactones
Dimers
Monomers
gonytolide C

ASJC Scopus subject areas

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

Cite this

Asymmetric Synthesis of Gonytolide A : Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling. / Wu, Xiaowei; Iwata, Takayuki; Scharf, Adam; Qin, Tian; Reichl, Kyle D.; Porco, John A.

In: Journal of the American Chemical Society, Vol. 140, No. 18, 09.05.2018, p. 5969-5975.

Research output: Contribution to journalArticle

Wu, Xiaowei ; Iwata, Takayuki ; Scharf, Adam ; Qin, Tian ; Reichl, Kyle D. ; Porco, John A. / Asymmetric Synthesis of Gonytolide A : Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling. In: Journal of the American Chemical Society. 2018 ; Vol. 140, No. 18. pp. 5969-5975.
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