Pavidolides A–E, new cembranoids from the soft coral Sinularia pavida

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

“…Compound 5 resembled most closely the recently reported cembranoid pavidolide A isolated from the soft coral Sinularia pavida [30] and a metabolite from Sarcophyton glaucum – methyl sarcoate reported by Ishitsuka et al [29] (see Fig. 7).…”

“…The new cembranoid 6,13-bisdesoxomethyl sarcoate ( 5 ) resembles most closely the methyl sarcoate described by Ishitsuka et al [29] from soft coral Sarcophyton glaucum and the pavidolide A (6-desoxomethyl sarcoate) isolated from Sinularia pavida [30]. Methyl sarcoate is reported to be a possible biosynthetic precursor of several biscembranoids, e.g., methyl sarcophytoate [47], a metabolite from S. glaucum and methyl neosartortuate from S. tortuosum [48].…”

“…Both related molecules and compound 5 have only one stereogenic center, i.e., at C-1. The reported absolute configuration of pavidolide A ([α] D 20 +124, c 0.25, CHCl 3 ) at C-1 is R [30]. The specific rotation value of 5 is +3.5 and does not allow indicating any configuration for C-1 in compound 5 .…”

Four New 7,8-Epoxycembranoids from a Chinese Soft Coral <i>Lobophytum</i> sp.

“…However, the interesting fact is that numerous structurally unique cembranoid derivatives have been continuously reported to enrich the cembranoid family in recent years. [7][8][9][10] Some of these metabolites have been confirmed to play important ecological roles in the life cycle of the corals, such as antifeeding, antifouling, and allelopathy properties, [9][10][11][12] while many of them are also described for biological activities of pharmacological significance, such as antitumor, antiviral, antimicrobial, and antiinflammatory activities. [1][2][3][4][5][6][7][8] All these findings indicate that natural cembranoids of marine origin still merit continuous attention for biomedical research.…”

Total Syntheses of (+)‐Sarcophytin, (+)‐Chatancin, (−)‐3‐Oxochatancin, and (−)‐Pavidolide B: A Divergent Approach

“…Theh ighly congested architectures as well as the intriguing biological properties of the sarcophytin family members have stimulated several elegant total syntheses of their core structures and target molecules from the groups of Gçssinger, [4a,e] Deslongchamps, [4b,f-j] Maimone [4c] and Carreira. [5] Preliminary investigation showed that 5 exhibits high selective inhibitory activity against an umber of human promyelocytic leukemia cell lines.T he dome-shaped [6,5,5,7] tetracyclic ring system, especially the fully functionalized cyclopentane core,c ombined with seven contiguous stereogenic centers renders 5 as ynthetic target with significant challenges.M ost recently, an exquisite enantioselective total synthesis toward 5 has been disclosed by Yang,G ong, and co-workers,a nd they employed ac ascade radical annulation of vinylcyclopropane as the key step. [5] Preliminary investigation showed that 5 exhibits high selective inhibitory activity against an umber of human promyelocytic leukemia cell lines.T he dome-shaped [6,5,5,7] tetracyclic ring system, especially the fully functionalized cyclopentane core,c ombined with seven contiguous stereogenic centers renders 5 as ynthetic target with significant challenges.M ost recently, an exquisite enantioselective total synthesis toward 5 has been disclosed by Yang,G ong, and co-workers,a nd they employed ac ascade radical annulation of vinylcyclopropane as the key step.…”