Organic & Biomolecular Chemistry Blog

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The article highlighted on the cover of our latest issue is work from Gautam Panda and Ritesh Singh at the Central Drug Research Institute, India.

They have reported an efficient, regioselective route to hetero [6,5,6]ABC tetrahydrofluorene cores.  This type of tricyclic hydrofluorene core is found in a class of natural products called Taiwaniaquinoids, which have shown some promising bioactivities.

To access the hetero tetrahydrofluorene skeleton the authors used divinyl alcohols, activated with Sc(OTf)3 in a Nazarov-type cyclisation achieving the desired scaffold under very mild conditions.

Application of Nazarov type electrocyclization to access [6,5,6] and [6,5,5] core embedded new polycycles: an easy entry to tetrahydrofluorene scaffolds related to Taiwaniaquinoids and C-nor-D homosteroids
Ritesh Singh and Gautam Panda
Org. Biomol. Chem., 2011, 9, 4782-4790
DOI: 10.1039/C0OB00892C