Aspidospermine, deacetyl

Conclusive evidence that the aliphatic portion of the pyrifolidine molecule was in fact identical with that of aspidospermine (II) was obtained from the mass spectra of their deacetyl derivatives (XLVII and VI, Table V). These proved to be identical, save only in the shift of 30 units observed in the peaks attributable to fragments containing the aromatic nucleus, this shift being due to the extra aromatic methoxyl group. 

Second, direct chemical proof of the aspidospermine skeleton was obtained by conversion of spegazzinidine dimethyl ether (LXX) to its tosylate (LXXIV) which on reduction with lithium aluminum hydride gave (— )-JVft-deacetyl-Xa-ethylpyrifolidine (LVII) identical, except for direction of rotation, with the product, (+ J-Xa-deacetyl- -ethyl-pyrifolidine (LVII), obtained by a similar reduction of (+ )-pyrifolidine (XLVI). Since (+ )-pyrifolidine is antipodal to aspidospermine (Section II, K), spegazzinidine has the same absolute configuration as aspidospermine (36). 

White quebracho contains 0.3-1.5% indole alkaloids, including aspidospermine, aspidos-permatine, aspidosamine, yohimbine (queb-rachine), /-quebrachamine, ebumamenine, aspidospermidine, /-pyrifolidine, deacetyl-pyrifolidine, rhazidine, and akuammidine, among others (glasby 1 list and horhammer ... 

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