Helvetica Chimica Acta p. 1935 - 1947 (1990)
Update date:2022-09-26
Topics:
Escher, Sina
Giersch, Wolfgang
Niclass, Yvan
Bernardinelli, Gerald
Ohloff, Guenther
The four possible A/B cis-fused diastereomers of Ambrox have been synthesized and their configurations and conformations established by X-ray and NMR analysis.Only 5β-ambrox (=1,2,3a,4,5,5aβ,6,7,8,9,9a,9bα-dodecahydro-3aβ,6,6,9aβ-tetramethylnaphtho<2,1-b>furan; 5) has an odor quality comparable to Ambrox.The 1,3-synperiplanar/diaxial conformation of the substituents at C(8) (=C(3a)) and C(10) (=C(9a)) has thus been confirmed to be a compulsory structure element for the particular odor.
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Doi:10.1016/0022-328X(90)80084-D
(1990)Doi:10.1055/s-1990-27073
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(1990)Doi:10.1016/S0040-4039(00)97024-2
(1990)Doi:10.1055/s-0030-1260787
(2011)Doi:10.1002/ejoc.201100289
(2011)
