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

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

ISBN-10: 0851863469

ISBN-13: 9780851863467

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1980, 21, 1921. Sesquiterpenoids 41 CH20H GlucO HO OH OH (271) (270) H02C* OH (272) * R (273) R (2741 R = = H OH \ OH OH (276) R (277) R (278) R = = = C1 OGluc OAllosyl (279) R' (280) R' (281) R' = = = CH20H, R2 = Me Me,R2 = CH20H C02H, R2 = Me A full report on the synthesis of dihydrofomannosin acetate (284) has been p ~ b l i s h e d . ' In ~ ~a follow-up paper on the biosynthesis of fomannosin (287), Cane and N a ~ h b e r have l ~ ~ used a number of incorporation experiments (particularly with [5,5-2H2]mevalonate)to show that fomannosin cannot be formed by the sequence (285) + (287) as shown in Scheme 28, since no deuterium incorporation could be detected at C-12.

Kurihara, J. Sasaki, and S. It6. Can. J. , 1979,57, 3,343. 02~6]undecylprecursors, (151) and (152), of gymnomitrol (144) as well as a-(153) and f3-barbatene (154). In a more recent paper74the trio1 (148) has been converted into bazzanene (155),which is considered to be the biogenetic precursor of the gyrnnornitrane class of sesquiterpenoids (Scheme 19). 1 111, LV ... ^^ Since the inter-relationships cannot be directly studied by proper biosynthetic methods the next best criterion for the validity of the postulated schemes is to study in vitro rearrangements which might simulate the in vivo pathways.

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 .

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A review of the literature published between September 1979 and August 1980 by J R Hanson; R B Boar; Royal Society of Chemistry.; et al


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