Yasuo Inubushi

Structure of dendrobine

Abstract From degradative and spectroscopic evidence, formula XXXI is proposed as the presumable structure of dendrobine and its stereochemical structure is shown in formula XXXIV or its mirror image.

Total synthesis of the lycopodium alkaloid (±)-serratinine

Serratinine (1) isolated from Lycopodium serratum Thunb. var. serratum f. serratum has been synthesized.

A new synthesis of spirovetivanes via the spiro acyloin intermediate

Ethyl-3-(1-ethoxycarbonyl-2,6-dimethylcyclohex-2-enyl)propionate 5 was stereoselectively synthesized. The diester 5 was spiroannulated by the acyloin condensation to give the bis(tri-methylsiloxy) ...

Triterpenoid constituents of Lycopodium phlegmaria L

From Lycopodium phlegmaria L. collected in Ceylon, eleven triterpenes, all of which belong to the serratenediol family, have been isolated. Serratenediol (I), serratenediol 3-acetate (II), serratriol (III), hydroxyserratenone (IV), and tohogenol (V) are known compounds. Phlegmanols A (VII), B (VIII), C (IX), D (X), E (XII), and phlegmaric acid (XI) are new compounds.

Studies on the alkaloids of menispermaceous plants. Part CCXLIX. Total synthesis of optically active natural isotetrandrine, phaeanthine, and tetrandrine

Natural phaeanthine (1a), isotetrandrine (lb), and tetrandrine (1c), belonging to the oxyacanthine–berbamine series of the bisbenzylisoquinoline alkaloids, have been synthesised by a stepwise route. One of the benzyliso-quinoline nuclei was constructed initially, and joined by the Ullmann method through ether linkages to protected phenethylamine and phenylacetic acid units. The phenylacetic acid portion was activated by formation of its nitrophenyl ester and condensed with the phenethylamine unit (protected by a t-butoxycarbonyl group) to form a macrocyclic amide. The latter was converted by Bischler-Napieralski cyclisation and reduction into the desired alkaloids without formation of any structural isomers.