Total synthesis of (−)-petrosiol E

Abstract

a b s t r a c t (À)-Petrosiol E, a metabolite of sponge Petrosia strongylata, has been synthesized in 32% overall yield from cheap natural D-xylose in 10 steps. Our strategy provides an efficient way for the total synthesis of other petrosiol members, featuring the three contiguous stereogenic centers are easily constructed from D-xylose chiral template.

An Important Function of Petrosiol E in Inducing the Differentiation of Neuronal Progenitors and in Protecting Them against Oxidative Stress

“…Petrosiol E Synthesis: Petrosiol E was synthesized from natural D-xylose in ten steps using the carbohydrate chiral template approach, and the detailed procedures were described in the previous report. [16] The compound purity used in this research met the elemental analysis requirement, i.e., 99.5% based on the high performance liquid chromatography (HPLC) detection. The chemical structure of Petrosiol E is depicted in Figure 1A.…”

“…Given their great value in pharmaceutics in translational medicine, several groups have been exerting great efforts to artificially synthesize these active natural products. We recently achieved the first total synthesis of (‐)‐Petrosiol E in ten steps starting from the chiral template D‐xylose with an overall yield of 32% . This efficient synthesis of Petrosiol E offers an opportunity to facilitate the mechanistic studies on its role in guiding neuron differentiation.…”

“…We recently achieved the first total synthesis of (-)-Petrosiol E in ten steps starting from the chiral template D-xylose with an overall yield of 32%. [16] This efficient synthesis of Petrosiol E offers an opportunity to facilitate the mechanistic studies on its role in guiding neuron differentiation. Thus far, several cell lines have been established for in vitro studies in neuroscience, including PC12 cells.…”

Synthesis and biological activities of petrosiols B and D

“…Regioselective oxidative cleavage of the terminal isopropylidene group in 15a,b was performed with periodic acid in dry ethyl acetate affording one-carbon diminished aldehyde, 20 which was immediately treated with CBr 4 /PPh 3 in DCM 21,22 to generate 1,L-dibromoalkenes 16a,b in about 51-52% yield. NaH-mediated dehydrobromination 12,23 of dibromoalkenes in wet THF at room temperature provided monobromoalkynes 6a,b in excellent yield. Cu(I)-catalyzed Cadiot-Chodkiewicz cross coupling of propargyl alcohol with monobromoalkynes 6a,b afforded the corresponding diynes 17a,b.…”

“…11 As part of our interests in the total synthesis of various complex natural products based on carbohydrate skeletons, we have reported the rst total synthesis of petrosiol E from D-xylose in 2014. 12 So far, there is no report regarding the syntheses of petrosiols B and C.…”