Two New Diterpene Isocyanides from a Sponge of the Family Adocidae

Marine Isonitriles and Their Related Compounds

“…Already in 1992, a kalihinene derivative with an open isoprenoid side chain was isolated by Sharma et al from a sample of Adocia sp. showing the same 2D structure but a different optical rotation ([α] D = +97° (CHCl 3 , c = 0.085)) compared to König’s compound [ 116 ]. Its relative configuration was not elucidated.…”

“…In 1992, a compound with an unusual amphilectane-framework in which ring C is spirocyclic to the cyclohexene ring was found by Sharma in a sponge of the Adociae family, collected off the island of Miyako (Japan, Figure 27 ). To date 7-isocyanoneoamphilecta-11,15-diene ( Neo1 ) remains the only known representative of its class [ 116 ].…”

Two Rare-Class Tricyclic Diterpenes with Antitubercular Activity from the Caribbean Sponge Svenzea flava. Application of Vibrational Circular Dichroism Spectroscopy for Determining Absolute Configuration

“…8 Among these polycyclic compounds, those that are based on the neoamphilectane and isoneoamphilectane scaffolds are considered exceptionally rare, and to this date, isocyanides 1 and 2 remain as the first and only known representatives of these families of marine-derived diterpenes, respectively. 9–11 Specifically, tricyclic compound 1 was isolated in 1992 by Higa and co-workers from a Japanese sponge of the family Adocidae, 9 whereas 2 , formally a 2(1→12)-abeoamphilectane, was isolated in 1996 by König et al from the tropical marine sponge Cymbastela hooperi . 10 Often, amphilectane-based diterpenes known to contain isocyanide and related functionalities are endowed with potent in vitro anti-malarial, anti-algal, anti-tubercular, anti-bacterial, anti-photosynthetic, anti-inflammatory, anti-proliferative, and anti-fouling activity.…”

Marine isocyano compounds

“…Both 10-isothiocyanatobiflora-4,15-diene (123) and 7-isocyanoneoamphilecta-t 1, t5-diene (124), isolated from a sponge in the family Adociidae [59], appear to bridge the amphilectane-cycloamphilectane and kalihinol-type skeletons (Sect. 4.2).…”

“…Metabolite 123 from Adociidae is interesting since the kalihinols isolated from several Acanthella species (vide supra) were first recognized to possess the biflorin skeleton E25]. The recent discovery of 123 and 124, the latter structure having been confirmed by X-ray crystallography [59], forms a link to the known tri-and tetracyclic amphilectanes (91)/cycloamphilectane (92) series.…”