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Marine prostanoids

Clavulones I and II are members of an unusual family of marine prostanoids from the coral Clavularia viridis which are biosynthesiied by a cationic (i.e. non-radical, non-endoperoxide) pathway. The total synthesis of clavulones I and II was accomplished from cyclopentadiene as SM goal. [Pg.303]

Epoxide ring-opening witli transfer of an sp carbon moiety was applied in a sbori syntliesis [44] of eicosanoid 56 [45], relevant in marine prostanoid biosyn-tliesis (Scheme 9.13). Honioallyl alcohol 55 was obtained in good yield from 54 by use of a cyano-G dman alketiylciiprate [46]. [Pg.300]

Iwashima, M. Okamoto, K. Miyai, Y. Iguchi, K. (1999) 4-Epiclavulones, new marine prostanoids fixm the Okinawan soft coral, Clavularia viridis. Chem. Phaim. Bull., 47, 884-6. [Pg.322]

Triclavulone 3, recently isolated from Ciavularia vulgaris, is one of the most complex of the family of about forty structurally-related fatty acid-derived marine prostanoids described from this species. Hisanaka Ito and Kazuo Iguchi of the Tokyo University of Pharmacy and Life Science recently reported (J. Am. Chem. Soc. 2004,126,4520) the total synthesis of 3, starting with the preparation of the enantiomerically-enriched bicyclic ketone 1. [Pg.56]

Watanabe K, Sekine M, Iguchi K (2003) Isolation of Three Marine Prostanoids, Possible Biosynthetic Intermediates for Clavulones, from the Okinawan Soft Coral Clavularia viridis. Chem Pharm Bull 51 909... [Pg.421]

Iwashima, M., Watanabe, K., and Iguche, K., New marine prostanoids, preclavulone lactones, from the Okinawan soft coral Clavularia viridis, Tetrahedron Lett., 38, 8319, 1997. [Pg.153]

Punaglandin 4 (PUG 4, 151, Figure 6.10) is one of the chlorinated marine prostanoids isolated from a Hawaiian octocoral, Telesto riisei, by Scheuer and coworkers in 1985. Its remarkable antitumor activity coupled with its unique structure attracted the attention of chemists, and its synthesis was achieved by Yamada, Noyori, Shibasaki, and Mori s groups. Our synthesis relied on lipase-catalysed asymmetric process, and is summarized in Figures 6.10 and 6.11.12... [Pg.232]

The marine prostanoid clavulone has been synthesized enantio-... [Pg.254]

Nagaoka, H., T. Miyakoshi, and Y. Yamada Total Synthesis of Marine Prostanoids Clavulones. Tetrahedron Lett. 25, 3621 (1984). [Pg.348]

Corey EJ, Matsuda SPT, Nagata R, Cleaver MB. Biosynthesis of 8(R)-HPETE and preclavulone A from arachidonate in several species of Caribbean coral. A widespread route to marine prostanoids. Tetrahedron Lett 1988 29 2555-2558. [Pg.12]

Asymmetric hydrolysis of a stereoisomeric mixture of ( )-53 with pig pancreatic lipase (PPL) afforded (lS,4P)-54 in 25% yield, which was indeed the theoretical yield. Other stereoisomers remained as the recovered 53 (Figure 24.27) [31]. Punaglandin 4, a marine prostanoid, was S5mthesized from (lS,4R)-54. [Pg.599]

Corey, E.J. and Matsuda, S.P.T. (1987) Generality of marine prostanoid biosynthesis by the 2-oxidopentadienyl cation pathway. Tetrahedron Lett., 28,4247-4250. [Pg.1373]

Iguchi, K Kaneta, S MorL K., Yamada, Y Honda, A., and Mori, Y. (1985) Chlorovulones new halogenated marine prostanoids with antitumor activity from stolonifer Clavularia viridis Quoy and Gaimard. Tetrahedron Lett, 26,5787-5790. [Pg.1379]

Nagaoka, H., Miyakoshi, T, and Yamada, Y. (1984) Total synthesis of marine prostanoids clavidones. Tetrahedron Lett., 25, 3621-3624. [Pg.1409]

Kuhn, C., Roulland, E., Madelmont, J.-C., Monneret, C., and Florent, J.-C. (2004) Synthesis and biological evaluation of new cross-conjugated dienone marine prostanoid analogues. Org. Biomd. Chem., 2, 2028-2039. [Pg.1415]


See other pages where Marine prostanoids is mentioned: [Pg.384]    [Pg.389]    [Pg.894]    [Pg.343]    [Pg.338]    [Pg.421]    [Pg.660]    [Pg.90]    [Pg.249]    [Pg.347]    [Pg.735]    [Pg.1386]    [Pg.70]   
See also in sourсe #XX -- [ Pg.687 ]

See also in sourсe #XX -- [ Pg.687 ]




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