Fernene

NHj F 1 h3c-c-ch-oh 1 1 h3c cn F fj CH-OH CN tiberschub an NH3 UberschuB an NH3 Methanol 30 rain NH3 einlci — ten bei —7SQ, dann 5 Woche 20-30 dann Solvetis ent-fernen und Hydrolyse mit 48% HBrin H20 2-Amino-3 fluor-3-methyl- propansdure Amino-( 1-fluor-cyclohexyl)-essigsaure 63 57 i... 

Adiantum boreale Presl. A. capillus-junonis Rupr. A. pedatum L. A. flabellulatum L. Tie Xian Jiu (Black maidenhair) Guo Tan Loan (Maidenhair fem) (root) Adipedatol, adiantone, hopadiene, isoadiantone, isofemene, fernene, gamma-femene, filicene, filicenal, femadiene.48 Treat cold and grippe. 

Adiantum capillus-junonis Rupr. China Adipedatol, adiantone, hopadiene, isoadiantone, isofemene, fernene, gamma-femene, filicene, filicenal, fernadiene.48 Treat cold and grippe. 

Blout (161) sowie Doty u. Mitarb. (162) berichteten liber einen ausgepragten Cotton-Effekt im fernen UV (Wendepunkt bei 190 m/i), der charakteristisch fiir Polypeptide mit Helixkonformation ist und einen schwachen negativen Cotton-Effekt bei Polypeptiden in der Knauelform. 

Wasserspuren lassen sich auch durch vorherige Umsetzung mit besonders reaktionsfahigen Halogeniden, z.B. TiCl4 423) oder NF3 424) von der Saule ent-fernen. Eine Methode zur Probeneinffihrung fester Metallchloride wird beschrieben425). 

Two new rearranged hopanes, alangidiol (178) and isoalangidiol (179), with a d-e cis fusion have been reported from the leaves of Alangium lamarckii. New fernene derivatives which have appeared this year include fern-9(l l)-en-6a-ol (180) and fern-9(ll)-en-20j8-ol (181) from the rhizomes of Polypodium juglandifolium and hortensol (182) from the leaves of Evodia hortensis The structure of (182) was confirmed by A"-ray analysis. 

BenzoyIamino-biphenyl Eine Looting von 1,0 g l-Benzoy]-lH-(benzotriazol) in 500 ml Benzo werden 4 Stdn. mit einer 200 W Quecksilbcr-Hochdruck-Lampe unter Stickstoff bcstrahlt. Nach Ent-fernen des Losungsmittels i. Vak. wird der Riickstand an Silikagel chromatographiert und mit 200 ml Dichlormethan eluicrt zunachst werden 600 mg unuingeselzles Triazol erhalten. Nach weiterer Elution mit 400 ml Dichlormethan werden 60 mg erhalten, die aus Ligroin umkristallisiert werden (F 88°) Aus-beute 15% d.Th.. 

Wilkins AL (1977) The structure of a triterpenoid ketol from Cetraria nivalis. Phytochemistry 16 608-609 Wilkins AL (1980) Nephrin structure and occurrence in Nephroma species. Phytochemistry 19 696-697 Wilkins AL, Elix JA (1990) New fernene triterpenes from the lichen Pseudocyphellaria aurata. Aust J Chem 43 623-627... 

Wilkins AL, Elix JA, Gaul KL, Moberg R (1989a) New hopane triterpenoids from lichens in the family Physciaceae. Aust J Chem 42 1415-1422 Wilkins AL, Elix JA, Gonzalez AG, Perez C (1989b) A one-and two-dimensional and C NMR study of some fernene triterpenoids. Aust J Chem 42 1185-1189 Wilkins AL, Elix JA, Whitton AA (1990) A one- and two-dimensional and C NMR study of some lichen triterpenoids of the pyxinol group. Aust J Chem 43 411-417... 

Gonzalez, Martin, and Perez 148) identified three new fernene derivatives from Xanthoria resendei 12a-acetoxy-3p-hydroxyfern-9(ll)-ene (498), 3p,12a-dihydroxyfern-9(l l)-ene (499) and 3,12-diketofern-9(l 1)-ene (500). The structures of these triterpenes were deduced from spectral evidence and confirmed by chemical interconversion and the Wolff-Kishner reduction of (500) to the parent fern-9(ll)-ene. 

Also from Lobaria species were isolated the new fernene derivatives retigeric acid A (125) and retigeric acid B (Takahashi et aL 1972). 

Wilkins AL, Elix JA, Gonzalez AG, Perez C (1989) A One- and Two-dimensional H and C-NMR Study of some Fernene Triterpenoids. Aust J Chem 42 1185... 

Feist s acid, A37 Fenchane, TIO a-fenchene, TIO a-fencholenic acid, TIO Fencholic acid, TIO Fenchone, TIO Fenchyl alcohols, TIO Fenfluramine, A5 Fernene, T44... 

Another noteworthy characteristic of this triterpene family is the frequent absence of an oxygen function at C3. Whereas greater than 98% of all other known C30 triterpenes possess a C3 oxygen grouping, about half of the fifty-four members of this particular class lack such functionality (7). The non-incorporation of squalene-2-3-oxide into A -fernene (together with a positive incorporation of squalene) supports the expectation that these non-oxygenated triterpenes are biosynthesized by a proton-initiated cyclization of squalene itself (496)> The incorporation of six tritium atoms into A -fernene from is consistent... 

The three fernene isomers (409, 413, and 414), all of which are natural triterpenes, and various functionalized variants thereof, suffer rearrangement in the retro-biogenetic direction to -neohopene (412) (501, 504—506). Evidently A -fernene (413) is relatively resistant to the acidic conditions since mixtures of (412) and (413) are often obtained. Both A -and A -fernene (414 and 409) are converted to the A -isomer under relatively mild conditions. The apparent ease of migration of the double bond into the A position in this series contrasts with the rapid rearrangement of multiflorenyl acetate (372-OAc) to P-amyrin acetate (352, R = OAc) mentioned in the preceding section. 

Ageta, H., K. Iwata, and K. Yonezawa Fern Constituents Fernene and Diploptene, Triterpenoid Hydrocarbons Isolated from Dryopteris crassirhizoma Nakai. Chem. Pharm. Bull. (Japan) 11, 408 (1963). 

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