Synthesis

Thallium (III)-mediated ring contraction of cis-octalins: An approach for the diastereoselective construction of the nor-bakkane skeleton

HMC Ferraz, TO Vieira, LF Silva

Index: Ferraz, Helena M. C.; Vieira, Tiago O.; Silva Jr., Luiz F. Synthesis, 2006 , # 16 p. 2748 - 2752

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Citation Number: 11

Abstract

Abstract A new approach for the diastereoselective synthesis of cis-hydrindanes bearing important structural features of the bakkane skeleton is described. The key step in such a sequence is a thallium trinitrate mediated oxidative rearrangement of cis-octalins. The ring- contraction products thus obtained were elaborated in a diastereoselective fashion into hydrindanes bearing a quaternary center.