By Myers C. N., Voegtlin C.
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G. by spontaneous air oxidation of a concentrated alcoholic solution (I34)], a reaction which was not noted for fungichromin or "lagosin"*. This difference was confirmed when filipin was found to contain no vicinal glycol group (no reaction with periodic acid) until after saponification of the lactone, which unmasked a glycol that consumed periodic acid with production of acetaldehyde and a pentaenal of Amax 386 mfl (IJ)· Since the filipin carbon chain could not be broken beyond the chromophore by periodic acid, a less selective reaction, nitric-acid oxidation, had to be resorted to: by this degradation, perhydrofilipin gave a mixture of acids whose largest identifiable member (by gas chromatography of the methyl esters) was iX-methyldodecanedioic acid (XV).
C=o (IlL) 13-Hydroxytetradecapentaenal. Chart 2. Alkaline Cleavage of Pimaricin. It will be observed that this single reaction, as formulated in Chart 2, involves no less than seventeen carbon atoms-half of the total number present in pimaricin. That the lactone ring does actually extend to the position shown, enclosing the entire polyene chain, would of course not be established by this reaction alone; in fact, no coercive evidence on this point was presented by the Lederle workers (89). However, there can be no doubt that PATRICK'S placement of the chromophore inside the lactone ring is correct, in the light of the complete structural solutions independently arrived at by the research teams of COPE (M.
Thus, the entire carbon skeleton was conclusively verified from this single derivative. ) 7,2I·Dimethyltritriacontane. CHa I HOCH2-CH-(CH2)9-CH-CH-CHa I I OH OH (XL) To locate the oxygen atoms, periodic acid fission (in this case, of perhydrofungichromin) was again resorted to. Lithium aluminum hydride reduction then gave two crystalline polyols, C19H400S and C15Ha20a, which could be deoxygenated to hydrocarbons identifiable by transpose mass spectrum as C6-C(CHa)-Cn and C-C(CHa)-C12. The eight hydroxyls of the C19-polyol could be located unambiguously on its carbon skeleton by the same two criteria previously mentioned, i.