Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Quinolizidines. XXI. Syntheses of (±) - and (-) -Alancines
TOZO FUJIIMASASHI OHBAASAKO YONEZAWAJUN SAKAGUCHI
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1987 年 35 巻 8 号 p. 3470-3474

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The first total synthesis of the Alangium alkaloid alancine (10) has been achieved in the form of a racemic modification by means of catalytic hydrogenolysis of the tricyclic amino acid (±) -9. Treatment of (±) -10 with aqueous HCl afforded the hydrochloride salt (±) -11. A parallel synthesis starting with (-) -9 gave (-) -alancine [(-) -10] as well as its hydrochloride [(-) -11] in good yields. The synthetic hydrochloride (-) -11 was found to be identical with a sample isolated from Alangium lamarckii THW., indicating that the natural sample, previously considered to be in the free base form [(-) -10], was actually in the hydrochloride form [(-) -11].
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© The Pharmaceutical Society of Japan
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