Algae Laurencia

Abe, T., Masuda, M., Suzuki, T. and Suzuki, M. 1999. Chemical races in the red alga Laurencia nipponica (Rhodomelaceae, Ceramales) Phycol. Res. 47 87-95. 

Amico, V., Caccamese, S., Neri, P., Russo, G. and Foti, M. 1991. BrasUane-type ses-quiterpenoids from the Mediterraanean red alga Laurencia obtusa. Phytochemistry 30 1921-1928. 

Oztunc, A., Imre, S., Loiter, H. and Wagner, H. 1991. Two C-15 bromoalleles form the red alga Laurencia obtusa. Phytochemistry 30 255-258. 

Suzuki, M. and Kurosawa, E. 1978. Two new halogenated sesquiterpenes from the red alga Laurencia majuscula. Tetrahedron Lett. 4805-4808. 

Kurosawa, E. and Kurata, K. 1987. Majusculone, a novel norchamigrane-type metabolite from the red alga Laurencia majuscula Harvey. Buh. Chem. Soc. Japan 60 3795-3796. 

Fukuzawa A, Masamune T (1981) Laurepinnacin and isolaurepinnacin, new acetylenic cyclic ethers from the marine red alga Laurenciapinnata Yamada. Tetrahedron Lett 22 4081 1084 Fukuzawa A, Kurosawa E, Tobetsu I (1979) Constituents of marine plants. XXXVI. Laurallene, new bromoallene from the marine red alga Laurencia nipponica yamada. Tetrahedron Lett 30 2797-2780... 

Sims JJ, Lin GHY, Wing RM (1974) Marine natural products. X. Elatol, a halogenated sesquiterpene alcohol from the red alga Laurencia elata. Tetrahedron Lett 39 3487-3490 Singh S, Kate BN, Banerjee UC (2005) Bioactive compounds from cyanobacteria and microalgae an overview. Crit Rev Biotechnol 25 73-95... 

The bromoallene (-)-kumausallene (62) was isolated in 1983 from the red alga Laurencia nipponica Yamada [64a], The synthesis of the racemic natural product by Overman and co-workers once again employed the SN2 -substitution of a propargyl mesylate with lithium dibromocuprate (Scheme 18.22) [79]. Thus, starting from the unsymmetrically substituted 2,6-dioxabicyclo[3.3.0]octane derivative 69, the first side chain was introduced by Swern oxidation and subsequent Sakurai reaction with the allylsilane 70. The resulting alcohol 71 was protected and the second side chain was attached via diastereoselective addition of a titanium acetylide. The synthesis was concluded by the introduction of two bromine atoms anti-selective S -substitution of the bulky propargyl mesylate 72 was followed by Appel bromination (tetrabromo-methane-triphenylphosphine) of the alcohol derived from deprotection of the bromoallene 73. 

Graciosallene (isolated from the red alga Laurencia obtusa) can be considered to be an opened 2,6-dioxabicydo[3.3.0]octane ... 

A recent X-ray crystallographic study has resulted in a revised structure (98) for nidifocene, a minor metabolite of the Hawaiian marine alga Laurencia nidifica. In the previous structure (Vol. 7, p. 69) the positions of chlorine and bromine were reversed. An extension of previous work on the non-enzymic biogenetic cyclization of geranyl and farnesyl diphenylphosphates has shown that (Z)-monocyclo-farnesyl diethylphosphate (99) can be converted into ( )-a-chamigrene (100) in... 

Caccamese, S. Amico, V. (1990) Two new rearranged sesquherpenoids from the red alga Laurencia obtusa. J. Nat. Prod., 53, 1287-96. 

Coll, J. Skelton, B.W. White, A.H. Wright, A.D. (1989) The structure detamination of two novel sesquiterpenes from the red alga Laurencia tenera. Aust. J. Chan., 42, 1695-703. 

San-Martin, A. Darias, J. Soto, H. Contraas, C. Herraa, J.S. Rovirosa, J. (1997) A new Cjs acetogenin from the marine alga Laurencia claviformis. Nat. Prod. Lett., 10,303-11. 

Takeda, S. limura, Y. Tanaka, K. Kurosawa, E. Suzuki, T. (1990) A new naturally occurring racemic ccnnpound from the marine red alga Laurencia obtusa. Chem. Lett., 155-6. 

Maru, N., Ohno, O., Koyama, T., Yamada, K., and Uemura, D. (2010b). Papillamide, a novel fatty acid amide from the red alga Laurencia papillosa. Chem. Lett. 39, 366-367. 

Laurepinnacin (23) and isolaurepinnacin (24) are acetylenic cyclic ethers from the red alga Laurencia pinnata Yamada that demonstrate insecticidal activity.47 Z-laureatin (25), Z-isolau-reatin (26), and deoxyprepacifenol (27) are other related compounds from the red alga... 

Elatol (134) from the red alga Laurencia rigida completely inhibits the settlement of Balanus amphitrite larvae at 0.1 pg/cm2 [107]. 

Parguerol triacetate (154) and deoxyparguerol acetate (155), diterpenoids from the red alga Laurencia saitoi, show potent feeding-deterrent activity against the herbivorous abalone Haliotis discus hannai and the sea urchin Strongylocentrotus nudus [120]. 

Two brominated C15 nonterpenoid compounds, japonenyne A (223) and B (224), with a novel 2,7-dioxabicyclo[4.3.0]nonane skeleton, have been isolated from the red alga Laurencia japonensis [172]. 

Double Sharpless epoxidation was also applied to the synthesis of a key intermediate 10 to the meso-compound 11 that is related to teurilene, abioactive polycyclic triterpene isolated from red alga Laurencia obtusa,4 The reaction of ( , )-Bisallylic alcohol 9 gave the bisglycidic alcohol 10 with 80% de and 89% ee for each epoxidation (Scheme 6AA.4). 

Masuda M, Abe T, Sato S, Suzuki T, Suzuki M (1997) Diversity of Halogenated Secondary Metabolites in the Red Alga Laurencia nipponica (Rhodomelaceae, Ceramiales). J Phycol 33 196... 

Erickson KL, Beutler JA, Gray GN, Cardellina II JH, Boyd MR (1995) Majapolene A, a Cytotoxic Peroxide, and Related Sesquiterpenes from the Red Alga Laurencia majuscula. J Nat Prod 58 1848... 

Kuniyoshi M, Marma MS, Higa T, Bemardinelli G, Jefford CW (2001) New Bromoter-penes from the Red Alga Laurencia luzonensis. J Nat Prod 64 696... 

Topcu G, Aydogmus Z, Imre S, Goren AC, Pezzuto JM, Clement JA, Kingston DGI (2003) Brominated Sesquiterpenes from the Red Alga Laurencia obtusa. J Nat Prod 66 1505... 

Brito I, Cueto M, Dorta E, Darias J (2002) Bromocyclococanol, a Halogenated Sesquiterpene with a Novel Carbon Skeleton from the Red Alga Laurencia obtusa. Tetrahedron Lett 43 2551... 

Juagdan EG, Kalidindi R, Scheuer P (1997) Two New Chamigranes from an Hawaiian Red Alga, Laurencia cartilaginea. Tetrahedron 53 521... 

Kimura J, Kamada N, Tsujimoto Y (1999) Fourteen Chamigrane Derivatives from a Red Alga, Laurencia nidifica. Bull Chem Soc Jpn 72 289... 

Suescun L, Mombru AW, Mariezcurrena RA, Davyt D, Fernandez R, Manta E (2001) Two Natural Products from the Algae Laurencia scoparia. Acta Cryst C57 286... 

Vairappan CS (2003) Potent Antibacterial Activity of Halogenated Metabolites from Malaysian Red Algae, Laurencia majuscula (Rhodomelaceae, Ceramiales). Biomol Engi-ner 20 255... 

Iliopoulou D, Roussis V, Pannecouque C, De Clercq E, Vagias C (2002) Halogenated Sesquiterpenes from the Red Alga Laurencia obtusa. Tetrahedron 58 6749... 

Kladi M, Xenaki H, Vagias C, Papazafiri P, Roussis V (2006) New Cytotoxic Sesquiterpenes from the Red Alga Laurencia obtusa and Laurencia microcladia. Tetrahedron 62 182... 

Sun J, HanLJ, Shi DY, FanX, WangSJ, Li S, Yang YC, Shi JG (2005) Sesquiterpenes from Red Alga Laurencia fristicha. Chin Chem Lett 16 1611... 

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