The structure of some antibiotics from the sponge

Rothberg, Irvin; Shubiak, Peter

doi:10.1016/s0040-4039(00)71979-4

“…42) and strobilinin () (Ref. 43) that present moreover the unsolve'structural problem of the stereochemistry of their double bonds (Scheme 6).…”

Section: Synthesis Of (-) (E)-y-bisabolene-89-epoxidementioning

confidence: 99%

Syntheses of marine molecules

Martı́n¹,

Palazón²,

Pérez³

et al. 1986

Pure and Applied Chemistry

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-The enantioselective total syntheses of (-)(E)ybisabolene-8,9-epoxide, (+) (2S,6R)-2-bromo-13-chamigrene, and (+)-chamigrene, important intermediates in the biosynthesis of natural sesquiterpenoids isolated from algae of the genus Laurencia, are described. The compounds are synthesized with regio ñd stereocontrol by using simple forms of bridged intermediates. This represents a general strategy for the enantioselective construction of spirol5.5lundecane systems containing a chiral quaternary center. Our recent current progress towards the synthesis of the biologically active C25 tetronic acids isolated from sponges of the genus Ircinia is also described.

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“…168 Quite a number of these compounds contain a tetronic acid moiety and show strong antibiotic activity against Staphylococcus aureus. These are exemplified by variabilin 239 from Ircinia variabilis, 169 its double-bond isomer strobilinin 240 from Ircinia strobilina, 170 and fasciculatin 241 from Ircinia fasciculata. 171 Compounds 242 and 243 occur in Ircinia dendroides.…”

Section: Furanoditerpenoidsmentioning

confidence: 99%

“…179 Two sesterterpenoids, 249 and 250, isolated from an Okinawa Ircinia species, were found to be moderately cytotoxic. 154 A re-investigation of the structure of strobilinin, originally isolated from Ircinia strobilina, 170 revealed that it consisted of two geometrical isomers, 251 and 252. 180 The structures of (18S)-ircinin-l 237, 168 (18S)-ircinin 2 238, 168 and strobilinins 251 and 252 have been tentatively assigned.…”

Section: Furanoditerpenoidsmentioning

confidence: 99%

Heterocyclic terpenes: linear furano- and pyrroloterpenoids

Liu

¹

,

Zhang

²

,

Abreu

³

2006

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“…168 Quite a number of these compounds contain a tetronic acid moiety and show strong antibiotic activity against Staphylococcus aureus. These are exemplified by variabilin 239 from Ircinia variabilis, 169 its double-bond isomer strobilinin 240 from Ircinia strobilina, 170 and fasciculatin 241 from Ircinia fasciculata.…”

mentioning

confidence: 99%

“…A re-investigation of the structure of strobilinin, originally isolated from Ircinia strobilina, 170 revealed that it consisted of two geometrical isomers, 251 and 252. 180 The structures of (18S)-ircinin-l 237, 168 (18S)-ircinin 2 238, 168 and strobilinins 251 and 252 have been tentatively assigned.…”

mentioning

confidence: 99%