Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Stereochemical Studies. XXXV. A Biogenetic-type Asymmetric Cyclization. Syntheses of optically Active α-Cyclocitral and trans-α-Damascone
MASAKATSU SHIBASAKISHIRO TERASHIMASHUNICHI YAMADA
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1975 Volume 23 Issue 2 Pages 279-284

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Abstract

Application of the biogenetic-type cyclization of citral (2) via its enamine, which was developed by us as described in the preceding paper, to the asymmetric synthesis, has been found to give (R) (+)-α-cyclocitral ((R) (+)-4) in at most 33% optical yield. (R) (+)-4 thus prepared was successfully converted to (R) (+)-trans-α-damascone ((R) (+)-6), a famous perfume which has fragrant odor, without racemization.

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© The Pharmaceutical Society of Japan
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