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 White, Qiang Shen, Jia Zhou

Research output: Contribution to journalArticle

25 Citations (Scopus)

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

Fingerprint

Kaurane Diterpenes
Diels-Alder reactions
Dimerization
Diterpenes
Cycloaddition Reaction
Electrons
dimerization
Cycloaddition
rings
Sulfides
synthesis
Biological Products
Antineoplastic Agents
electrons
cycloaddition
sulfides
ethers
products

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels-Alder reactions : Synthesis of dihydropyran-fused diterpenoids. / Ding, Chunyong; Wang, Lili; Chen, Haijun; Wild, Christopher; Ye, Na; Ding, Ye; Wang, Tianzhi; White, Mark; Shen, Qiang; Zhou, Jia.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 42, 14.11.2014, p. 8442-8452.

Research output: Contribution to journalArticle

Ding, Chunyong ; Wang, Lili ; Chen, Haijun ; Wild, Christopher ; Ye, Na ; Ding, Ye ; Wang, Tianzhi ; White, Mark ; Shen, Qiang ; Zhou, Jia. / Ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels-Alder reactions : Synthesis of dihydropyran-fused diterpenoids. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 42. pp. 8442-8452.
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