Intramolecular Diels-Alder cycloadditions of fulvenes. Application to the kigelinol, neoamphilectane, and kempane skeletons

Bor-Cherng Hong; Fon-Len Chen; Shang-Hung Chen; Ju-Hsiou Liao; Gene-Hsiang Lee

doi:10.1021/ol047730m

Intramolecular Diels-Alder cycloadditions of fulvenes. Application to the kigelinol, neoamphilectane, and kempane skeletons

Org Lett. 2005 Feb 17;7(4):557-60. doi: 10.1021/ol047730m.

Authors

Bor-Cherng Hong¹, Fon-Len Chen, Shang-Hung Chen, Ju-Hsiou Liao, Gene-Hsiang Lee

Affiliation

¹ Department of Chemistry, National Chung Cheng University, Chia-Yi, 621 Taiwan, R.O.C. chebch@ccu.edu.tw

PMID: 15704893
DOI: 10.1021/ol047730m

Abstract

A variety of polycyclic ring skeletons (e.g., kigelinol, neoamphilectane, and kempene systems) can be prepared rapidly via intramolecular Diels-Alder cycloadditions (IMDA) of fulvenes. The length of the tethers and the diversity of the substituents on the fulvene core dictate the nature of the IMDA pathway. [reaction: see text]

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Cyclopentanes / chemical synthesis*
Furans / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Polycyclic Aromatic Hydrocarbons / chemical synthesis*

Substances

Cyclopentanes
Furans
Polycyclic Aromatic Hydrocarbons
kigelinone
fulvene