Bu₂BOTf: A Powerful Tool in Stereoselective Synthesis

The Natural Products Chemistry of the Gorgonian Genus Pseudopterogorgia (Octocorallia: Gorgoniidae)

“…272 Dinoflagellates are now a confirmed source of amphilectane (Pss), serrulatane (seco-pseudopterosins) and pseudopterane (kallolides) diterpenes, which were originally extracted from corals. An example is pseudopterosin Q (17), which was shown to be very toxic against HSV-1 and HSV-2 (EC 50 ¼ 2.9 mmol l À1 ), with SI values of <2.4. While Kerr and coworkers have presented a few examples in which bioactive Pseudopterogorgia metabolites are produced by symbiotic microorganisms, it is conceivable that these are probably the exception rather than the rule.…”

“…During 2004, in separate but nearly synchronous works, the research groups of Ata (Manitoba, Canada), Duque (Bogota, Colombia), and Rodríguez (San Juan, Puerto Rico) reported 14 new diterpene glycosides from P. elisabethae specimens collected in the Bahamas and Providencia Island, Colombia, namely pseudopterosins P-Y (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29). Such coincidence unwittingly led to duplication in structures and trivial names.…”

“…Such coincidence unwittingly led to duplication in structures and trivial names. As part of an investigation to determine Ps composition and concentration in colonies of P. elisabethae from the islands of San Andrés and Providencia, 60 the Colombian group described the isolation and structure elucidation of seven new compounds, pseudopterosins P-V (16)(17)(18)(19)(20)(21)(22), along with the known pseudopterosins G (7) and K (11), 58 whereas the Puerto Rican group reported exactly the same new compounds, except for pseudopterosin S (19), from P. elisabethae specimens collected at the same location. [58][59][60][61] The revised names are used throughout this review.)…”

“…[87][88][89][90] The subsequent coisolation of 7-hydroxyerogorgiane (61) and 7,8-dihydroxyerogorgiaene (62) from an extract of Floridian P. elisabethae led Ferns and Kerr to propose the intermediacy of these compounds in Ps biosynthesis. [100][101][102][103] The tricyclic cis, trans-fused 5,6,6 ring system of elisabethin A embodies a fully substituted enedione functionality and six contiguous stereogenic centers, of which one, at the junction of the three rings, is quaternary. 76 Analysis of mass spectral, UV/VIS (ultraviolet/visible), and 13 C-NMR data indicated that compounds 63-65 were bicyclic p-benzoquinones with an ortho hydroxyl functionality.…”