Sarcophytin, A Novel Tetracyclic Diterpenoid From The Indian Ocean Soft Coral Sarcophyton elegans

Trocheliophorin: A novel rearranged sesquiterpenoid from the Indian Ocean soft coralSarcophyton trocheliophorum

“…This species, which occurs in different sea waters, has been chemically examined [11 -14]. The present chemical examination of this Indian species furnished a novel carboxylic acid, trocheliophorin (1), along with the known diterpenoid sarcophytin (3) [6], methyl arachidonate, and two polyhydroxy steroids, (24S)-24-methylcholestane-3b,5a,6b,25-tetrol-25-mono acetate and (24S)-24-methylcholestane-3b,5a,6b,25-tetrol. The structure of the novel acid was elucidated by a study of its physical and spectral ( 1 H, 13 C, APT, 1 H-1 H COSY; HMQC, HMBC and Mass) data.…”

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

“…[1] Since the first discovery of (+ +)-sarcophytin (1)b y Anjaneyulu and co-workers from Sarcophyton elegans in 1998 ( Figure 1), [2] av ariety of additional sarcophytin family members have been isolated, and their primary biological function is believed to be chemical defense against predators. [1] Since the first discovery of (+ +)-sarcophytin (1)b y Anjaneyulu and co-workers from Sarcophyton elegans in 1998 ( Figure 1), [2] av ariety of additional sarcophytin family members have been isolated, and their primary biological function is believed to be chemical defense against predators.…”

“…[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. Therefore,asystematic investigation on the collective synthesis of these cembranoids is highly desirable to shed light on the biosynthetic relationship between their polycyclic skeletons.H erein, we describe our efforts in this field which culminated in the concise and divergent total syntheses of (+ +)-sarcophytin (1), (+ +)-chatancin (3), (À)-3-oxo-chatancin (4), and (À)-pavidolide B(5), as well as the structural revision of (À)-isosarcophytin (2). Therefore,asystematic investigation on the collective synthesis of these cembranoids is highly desirable to shed light on the biosynthetic relationship between their polycyclic skeletons.H erein, we describe our efforts in this field which culminated in the concise and divergent total syntheses of (+ +)-sarcophytin (1), (+ +)-chatancin (3), (À)-3-oxo-chatancin (4), and (À)-pavidolide B(5), as well as the structural revision of (À)-isosarcophytin (2).…”

“…Marine corals continue to capture the attention of chemists as ar ich source of structurally diverse cembrane diterpenoids. [1] Since the first discovery of (+ +)-sarcophytin (1)b y Anjaneyulu and co-workers from Sarcophyton elegans in 1998 ( Figure 1), [2] av ariety of additional sarcophytin family members have been isolated, and their primary biological function is believed to be chemical defense against predators. [3] Among them, (+ +)-chatancin (3)w as revealed as ap otent platelet-activating factor (PAF) antagonist.…”

Short, Enantioselective Total Synthesis of Chatancin

“…[3] Chatancin bears striking structural resemblance to the diterpene sarcophytin ( 2 ), isolated from a geographically far-removed Sarcophyton species. [6] …”