A review of the literature published between September 1979 by J R Hanson; R B Boar; Royal Society of Chemistry.; et al

By J R Hanson; R B Boar; Royal Society of Chemistry.; et al

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By J R Hanson; R B Boar; Royal Society of Chemistry.; et al

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Chem. Perkin, Trans. 1, 1975, 1574. 63 W. C. -Y. Tsai, J. A m . CFem. , 1980, 102, 3654. 64 W. R. Roush and T. E. D'Ambra, J. Org. , 1980,45,3927. 65 W. K. Anderson and G. E. Lee, J. Org. , 1980,45,501. 66 W. K. Anderson and G. E. Lee, J. Med. , 1980,23,96. 67 A . J. Pearson and P. R. Raithby, J. Chem. ,Perkin Trans. 1, 1980, 395. " C. W. Ong and A . J. , 1980, 21, 2349. 62 19 Sesq u ite rpen oids 1 .. OH - HO'H THPO' (135) Reagents: i, MCPBA-NaHCO,; HS(CH,),SHBF,; vi, 0 ii, HC0,Bu'-KOBu'; iii, MVK-KOBu'; iv, NaBH,; - H+;vii, Bu',AlH; viii, NBS-collidine; ix, KOH-MeOH; x Scheme 13 Me0 Me0 (136) R (138) R = = 'R OAc H (137) v, MeLi; xi, H,O' Sesquiterpen oids 21 Within the space of two months, no fewer than five independent syntheses of the liverwort sesquiterpenoid gymnomitrol (144)have been r e p ~ r t e d .

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. Gombatz, T. Harayama, E. Berman, and P. F. Schuda, J. A m . H. Parsons, R. H. Schlessinger, and M. L. Quesada, J. A m . Chem. , 1980,102,889. Bohlmann, N. L. Van, T. 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.

Stipanovic, A. A. Bell, and D. H. O’Brien, Phyrochemistry, 1980,19, 1735. M. A. Ferreira, T. J. King, S. Ali, and R. H. Thomson, J. Chem. , Perkin Trans. 1, 1980, 249. Terpenoids and Steroids 30 O m o H H i A (194) R’ = R2 = H (195) R’ = H , R 2 = OH (196) R’,R2 = 0 A , (197) previously known compound gmelofuran. These eight compounds have also been identified as constituents of the heartwood of the related species H. tiliaceus (from Fiji and Sri Lanka). ’~ The data for this compound correspond closely to those given for hibiscone B (195) and hence they may be identical, in which case a structural revision is required.

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