A tandem, nitroalkene conjugate addition/[3+2] cycloaddition approach to the synthesis of the pentacyclic core of (±)-scandine

Scott E. Denmark, Jeromy J. Cottell

Research output: Contribution to journalArticle

Abstract

The complete pentacyclic core of the melodinus alkaloid scandine has been synthesized. The synthetic strategy features two key steps: (1) a tandem nitroalkene conjugate addition/[3+2] cycloaddition of the resulting silyl nitronate and (2) an intramolecular Heck reaction of an aryl iodide with a γ-disubstituted allylic alcohol which set a highly congested, quaternary stereogenic center with the concomitant formation of an aldehyde. Intramolecular reductive amination with this aldehyde completed the pentacyclic core.

Original languageEnglish (US)
Pages (from-to)2397-2402
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number16-17
DOIs
StatePublished - Nov 1 2006

Fingerprint

Cycloaddition
Aldehydes
Amination
Alkaloids
Iodides
Alcohols
allyl alcohol

Keywords

  • Conjugate addition
  • Nitroalkenes
  • Quaternary stereogenic centers
  • Silyl nitronates
  • [3+2] cycloaddition

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

A tandem, nitroalkene conjugate addition/[3+2] cycloaddition approach to the synthesis of the pentacyclic core of (±)-scandine. / Denmark, Scott E.; Cottell, Jeromy J.

In: Advanced Synthesis and Catalysis, Vol. 348, No. 16-17, 01.11.2006, p. 2397-2402.

Research output: Contribution to journalArticle

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