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Issue 42, 2014
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ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels–Alder reactions: synthesis of dihydropyran-fused diterpenoids

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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.

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

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Article information


Submitted
20 May 2014
Accepted
01 Sep 2014
First published
02 Sep 2014

Org. Biomol. Chem., 2014,12, 8442-8452
Article type
Paper
Author version available

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

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