Application of the Rodriguez-Pattenden Photo-Ring Contraction: Total Synthesis and Configurational Reassignment of 11-Gorgiacerol and 11-Epigorgiacerol

Weinstabl, Harald; Gaich, Tanja; Mulzer, Johann

Org. Lett. 2012, 14(11), 2834-2837.

A stereospecific photochemical ring contraction was used as the key step in the first total synthesis of the marine pseudopteranyl diterpene 11-gorgiacerol and its 11-epimer. The synthesis allowed the correction of the configurations that had been misassigned in the literature. In addition, some novel pseudopteranyl derivatives have been made.