Jump to main content
Jump to site search

Issue 42, 2014
Previous Article Next Article

ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels–Alder reactions: synthesis of dihydropyran-fused diterpenoids

Author affiliations

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.

Graphical abstract: ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels–Alder reactions: synthesis of dihydropyran-fused diterpenoids

Back to tab navigation

Supplementary files

Publication details

The article was received on 20 May 2014, accepted on 01 Sep 2014 and first published on 02 Sep 2014


Article type: Paper
DOI: 10.1039/C4OB01040J
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 8442-8452
  •   Request permissions

    ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels–Alder reactions: synthesis of dihydropyran-fused diterpenoids

    C. Ding, L. Wang, H. Chen, C. Wild, N. Ye, Y. Ding, T. Wang, M. A. White, Q. Shen and J. Zhou, Org. Biomol. Chem., 2014, 12, 8442
    DOI: 10.1039/C4OB01040J

Search articles by author

Spotlight

Advertisements