Synthesis of d,l-Norlabdane Oxide and Related Odorants: An Intramolecular Radical Approach
The Journal of Organic Chemistry1998Vol. 63(14), pp. 4779–4785
Citations Over TimeTop 13% of 1998 papers
Abstract
A cascade radical approach to d,l-norlabdane oxide and related odorants is reported. Oxidative radical cyclization of polyene 4 with Mn(III) and Cu(II) afforded exclusively bicycle 3, which upon acid treatment gave tricycle 2 possessing the norlabdane oxide skeleton with a modified A-ring system. Tricycle 2 was ultimately converted to d,l-norlabdane oxide 1 and to several new A-ring labdane oxides as potential odorants.
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