The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available d-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI2-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes.

Short and efficient syntheses of two diastereomeric cyclopentane segments present in most jatrophane diterpenes were achieved. Key steps are a stereoselective C-2 elongation, an RCM, and a hydroboration reaction. An orthogonal protecting group methodology makes these segments useful building blocks for diterpene synthesis.

The bark of the rain forest tree Galbulimima belgraveana has been identified as a rich source of fascinating natural products and so far 28 unique alkaloids have been isolated. The chemical interest in Galbulimima alkaloids started with the discovery of the promising biological activities of himbacine. Fifteen years after the first total synthesis of himbacine, this class of natural product still inspires, with the structurally more complex congeners himandrine, himgaline, and G.B. 13 as highly challenging synthetic targets. This review article summarizes and discusses all syntheses of Galbulimima alkaloids published to date.

Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl‐3 starting from (1R,5S)‐bicyclo[3.2.0]hept‐2‐en‐6‐one is described. Key steps in the sequence include a Baeyer–Villiger oxidation, an iodolactonization reaction, and the installation of the northern side chain through the addition of a lithiated vinyl bromide. The overall efficiency of the route is increased by taking advantage of latent symmetry.

A short and efficient synthesis of the cyclopentane moiety of the jatrophane diterpene Pl-3 has been developed. The route features an enyne metathesis reaction, and a stereoselective palladium-catalyzed reductive epoxide opening as key steps.