Synthesis of a trans,syn,trans-dodecahydrophenanthrene via a bicyclic transannular Diels-Alder reaction: intermediate for the synthesis of fusidic acid. Academic Article uri icon

abstract

  • While thermolysis of the macrobicyclic triene lactone 12 did not produce the expected bicyclic transannular Diels-Alder (BTADA) product 13, heating the corresponding ether 18 to 110 C for 4 h afforded a quantitative yield of the desired cycloadduct 19, which could be easily reduced to the perhydrophenanthrene, an ABC ring analogue of fusidic acid 1. Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does.

published proceedings

  • J Org Chem

author list (cited authors)

  • Jung, M. E., Zhang, T., Lui, R. M., Gutierrez, O., & Houk, K. N.

complete list of authors

  • Jung, Michael E||Zhang, Ting-Hu||Lui, Rebecca M||Gutierrez, Osvaldo||Houk, KN

publication date

  • January 2010