By J R Hanson; R B Boar; Royal Society of Chemistry.; et al
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Extra resources for A review of the literature published between September 1979 and August 1980
OH 4 2Me . C02Me lxiv-xvi \\ H Lo/ L O ) OMe 0 0 0 ,CO,Et Reagents: i, LDA; ii, CH,=CHCH,Br; iii, ==)) (319) [ ; iv, NaH-OC(OMe),; v, KN(SiMeJ,; vi, CO,; C0,Et vii, H,O'; viii, CH,N,; ix, NaBH,; x, MsCl-Et3N; xi, collidine, A; xii. 14' In certain of the species this compound co-occurs with the previously known isomer isocomene (32 1) and modhephene (322). These three hydrocarbons also co-occur in the roots of some Silphium (320) (321) R (322) R = H (323) R = OAc 143 S. Danishefsky, M. Hirama, K.
V. C. Pham, J. Jacupovic, A. Schuster, V. Zabel, and W. H. Watson, Chem. , 1979,101,7020. 145 Phytochemistry, 1979,18,1831. '46 It is suggested that these novel compounds could be derived from the cation generated from caryophyllene (324) as shown in Scheme37. Two (327) R' = M e , R 2 = H (328) R' = H , R 2 = Me Scheme 37 oxygenated derivatives, 13-acetoxymodhephene (323) and 5-0x0-5,6Hsilphiperfolene (329), have been isolated from the roots of Liabum ~pecies,'~' and arnicenone (330), an isocomene derivative, occurs in the rhizomes and roots -T (Q' (329) 146 147 0 a 4-o (330) F.
SOC. , 1980, 53, 160. D. E. Cane and R. B. , 1980, 21,437. J. R. Hanson, T. Marten, and R. Nyfeler, J. Chem. ,Perkin Trans. I , 1976, 876. H H (288) Scheme 28 derived from the pro-5R hydrogen of mevalonate, but it is not absolutely clear whether this hydrogen originates from C-1 or C-9 of farnesyl pyrophosphate. '27These compounds cooccur with a number of other known vellerane sesquiterpenoids which have been isolated previously from Lacturius species. Two related compounds, blennin A (297) and blennin D (298), have been isolated from Lucturius blennius.