Total synthesis of sparstolonin B via a palladium-catalyzed aldehyde α-arylation

Dalton Kim, Aaron Nash, Jef De Brabander, Uttam K. Tambar

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A concise and convergent total synthesis of sparstolonin B was developed. A palladium-catalyzed aldehyde α-arylation was utilized to construct the carbon skeleton of the natural product. A subsequent simple one-pot procedure effected global deprotection and closure of the final two rings via an unusual autoredox mechanism for the conversion of a bis-hydroquinone intermediate to the natural product. The 6 step synthetic sequence was realized in 18% overall yield.

Original languageEnglish (US)
JournalTetrahedron
DOIs
StateAccepted/In press - Jan 1 2018

Fingerprint

Palladium
Biological Products
Aldehydes
Skeleton
Carbon
sparstolonin B
hydroquinone

Keywords

  • Arylation
  • Autoredox
  • Cross-coupling
  • Palladium catalysis
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Total synthesis of sparstolonin B via a palladium-catalyzed aldehyde α-arylation. / Kim, Dalton; Nash, Aaron; De Brabander, Jef; Tambar, Uttam K.

In: Tetrahedron, 01.01.2018.

Research output: Contribution to journalArticle

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