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

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

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

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

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

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

A Non-Photochemical Approach to the Bicyclo[3.2.0]heptane Core of Bielschowskysin

An asymmetric synthesis of the tricyclic core (−)-<b>1</b> of the marine diterpene bielschowskysin is described. In particular, a methodology was developed to introduce the crucial quaternary center at C-12

A Non-Photochemical Approach to the Bicyclo[3.2.0]heptane Core of Bielschowskysin

An asymmetric synthesis of the tricyclic core (−)-<b>1</b> of the marine diterpene bielschowskysin is described. In particular, a methodology was developed to introduce the crucial quaternary center at C-12

A Short Access to the Skeleton of Elisabethin A and Formal Syntheses of Elisapterosin B and Colombiasin A

A short stereoselective synthesis of the Elisabethin A skeleton <b>4</b> is described, which opens a formal access to the diterpenes Elisapterosin B and Colombiasin A as well. Key reactions were an intermolecular <i>endo</i>-selective Diels–Alder reaction to generate the decalin part of the molecule, a chemo- and diastereoselective allylation of an aldehyde with allylzinc, a palladium ene annulation of the cyclopentane ring, and a novel sulfonium ylide induced fragmentation of a polycyclic ketone. Additional insights have been gained for the crucial epimerization at C-2