Oxidative polycyclization with rhenium(VII) oxides: application of the stereoselectivity rules in the total synthesis of rollidecins C and D

Rollidecin C, 1, and rollidecin D, 2, two adjacent bis-THF Annonaceous acetogenins, were synthesized from the partially functionalized 'naked' carbon skeletons 14 and 15, respectively. The retrosynthetic route to the target compounds was guided by the recently proposed rules of stereoselectivity for the tandem oxidative cyclization reaction with trifluoroacetylperrhenate. Thus, the rapid transformation of compounds 14 and 15 to 1 and 2, respectively, was achieved with a predictable stereochemistry by the oxidative-bis-cyclization with Re(VII) followed by one or two simple transformations. (C) 2001 Elsevier Science Ltd. All rights reserved.