Synthesis of sesquiterpene from centaurea species - 4,9-dioxo-bisabol-2,7(14),10-triene and its analogues

Abstract

Reactions of 10-chlorocarvone or 10-chlorodihydrocarvone with isopentenal or isopentanal in the presence of zinc dust yielded homoallylic alcs. I, II, and III. I-III were oxidized to 4,9-dioxobisabol-2,7(14),10-triene, 4,9-dioxobisabol-7(14),10-diene and 4,9-dioxobisabol-7(14)-ene resp. by chromium trioxide-pyridine complex. 4,9-Dioxobisabol-7E,10-diene was obtained from dihydrocarvone acetal allyl lithium species and isopentenal via a sequence of reactions.

Key words: MONOCYCLIC SESQUITERPENE, ORGANIC SYNTHESIS, POLYENE P, ETHANEDIAMINE P, CENTAUREA SPECIES, BISABOLONE

CLC Number:

O629

Cite this article

DONG GENGWEI;FAN WEIMING;YUAN WEIMIN;JIA YUNYI. Synthesis of sesquiterpene from centaurea species - 4,9-dioxo-bisabol-2,7(14),10-triene and its analogues[J]. Chin. J. Org. Chem., 1989, 9(1): 65-68.

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矢车菊中倍半萜 - 4,9-二氧-红没药-2,7(14), 10-三烯及其类似物的合成