Ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels-Alder reactions: Synthesis of dihydropyran-fused diterpenoids

Chunyong Ding, Lili Wang, Haijun Chen, Christopher Wild, Na Ye, Ye Ding, Tianzhi Wang, Mark A. White, Qiang Shen, Jia Zhou

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Abstract

A mild and concise approach for the construction of a 3,4-dihydro-2H-pyran ring integrated into the A-ring of the natural product oridonin using an optimized inverse electron demand hetero-Diels-Alder (IED HDA) reaction is reported herein. A self-dimerization of the exocyclic enone installed in the A-ring through a homo-HDA reaction was identified to exclusively give a dimeric ent-kaurane diterpenoid with the spirochroman core. Moreover, efficient cross-HDA cycloadditions of this enone with various vinyl ethers or vinyl sulfides, instead of its own homo-HDA dimerization, were achieved in a regio- and stereoselective manner, thus providing access to novel dihydropyran-fused diterpenoids as potential anticancer agents to overcome chemoresistance. This journal is

Original languageEnglish (US)
Pages (from-to)8442-8452
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number42
DOIs
StatePublished - Nov 14 2014

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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