Quinolizidine alkaloid 7-hydroxy

In a similar manner, the 2-cyano-6-oxazolopiperidine synthon is useful for the chiral synthesis of in-dolizidine (monomerine piperidine [(+)- and (-)-coniine and dihydropinidine] and quinolizidine alkaloids.2-Hydroxymethyl-1-amino-1-cyclopropanecarboxylic acid (-)-(2I )-hydroxy-(3S)-nonylamine and a-substituted phenylethylamines are obtained in optically active form from (-)-N-cyanomethyl-4-phenyloxazolidine. 

C.sHjjNjO, Mr 246.35, mp. 108-109 °C, [a]g -317° (CHgOH). A quinolizidine alkaloid of the sparteine type from some Lupinus species and Cadia ellisiana (Fabaceae). Analogous to lupanine a I3a-hydroxy derivative (C15H22N2O2, Mr 262.35) of M. is also known. It is found in Lupinus albus and L. cosentinii. A depressive activity of M. on the central nervous system has been described. ... 

Lupinus sericeus contains (—)-7-hydroxy-p-isosparteine and 10, 17-dioxo-P-isosparteine, which are also sparteines tetracyclic quinolizidine alkaloids with a quinolizidine nucleus. Moreover, other alkaloids from this group include epiaphylline and aphylline, alkaloids from L. latifolius, and (—)-lindenianine, an alkaloid from Lupinus lindenianus and Lupinus verbasciformis. Nuttalline (4p-hydroxy-2-oxosparteine) is a tetracyclic quinolizidine alkaloid from Lupinus nuttalli An alkaloid, sparteine can be converted to a-isosparteine or p-isosparteine, which occurs particularly in Cytisophyllum sessilifolium In contrast to aphylline, 17-oxosparteine is known to be s5mthesized only under energetic conditions. ... 

Hydroxy lysine, dehy d rolysino-norleucine. desmosine, pipecolic acid, mimosine. piperidine and quinolizidine alkaloids... 

As regards the 21 benzo[a]quinolizidine-type Alangium alkaloids, they can be structurally classified into four types according to their substitution patterns in the aromatic ring A (i) 9,10-dimethoxy type (72), (ii) 8-hydroxy-9,10-dimethoxy type (73), (iii) 9-hydroxy-lO-methoxy type (74), and (iv) 10-hydroxy-9-methoxy type (75) 7,10,16). Thus, type 72 includes 10 alkaloids... 

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