The conversion of (−)- and (+)-dihydrocarvone into chiral intermediates for the synthesis of (−)-polygodial, (−)-warburganal and (−)-muzigadial
Publication type: Journal Article
Publication date: 1989-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
(−)-Dihydrocarvone was converted into (−)-(4aR, 8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a, 8,8-trimethylnaphthalene-2(H)-one ( 1 ) via an efficient route in which a Wolff-Kishner reduction, accompanied with a double bond isomerisation brought on a major simplification. Ketone 1 is a suitable intermediate for the syntheses of the insectantifeedants (−)-polygodial and (−)-warburganal. (+)-Dihydrocarvone was converted into (+)-(4aR, 7S, 8aR)-4a,7-dimethyl-8-methylene-3, 4,4a,5,6,7,8,8a-octahydronaphthalene-2( 1H )-one ( 2 ), an intermediate ketone for the synthesis of (−)-muzigadial.
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Total citations:
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Citations from 2024:
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(4.66%)
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Jansen B. J., Kreuger J. A., de Groot A. The conversion of (−)- and (+)-dihydrocarvone into chiral intermediates for the synthesis of (−)-polygodial, (−)-warburganal and (−)-muzigadial // Tetrahedron. 1989. Vol. 45. No. 5. pp. 1447-1452.
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Jansen B. J., Kreuger J. A., de Groot A. The conversion of (−)- and (+)-dihydrocarvone into chiral intermediates for the synthesis of (−)-polygodial, (−)-warburganal and (−)-muzigadial // Tetrahedron. 1989. Vol. 45. No. 5. pp. 1447-1452.
Cite this
RIS
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TY - JOUR
DO - 10.1016/0040-4020(89)80143-7
UR - https://doi.org/10.1016/0040-4020(89)80143-7
TI - The conversion of (−)- and (+)-dihydrocarvone into chiral intermediates for the synthesis of (−)-polygodial, (−)-warburganal and (−)-muzigadial
T2 - Tetrahedron
AU - Jansen, Ben J.M
AU - Kreuger, Jacoba A
AU - de Groot, Aede
PY - 1989
DA - 1989/01/01
PB - Elsevier
SP - 1447-1452
IS - 5
VL - 45
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1989_Jansen,
author = {Ben J.M Jansen and Jacoba A Kreuger and Aede de Groot},
title = {The conversion of (−)- and (+)-dihydrocarvone into chiral intermediates for the synthesis of (−)-polygodial, (−)-warburganal and (−)-muzigadial},
journal = {Tetrahedron},
year = {1989},
volume = {45},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/0040-4020(89)80143-7},
number = {5},
pages = {1447--1452},
doi = {10.1016/0040-4020(89)80143-7}
}
Cite this
MLA
Copy
Jansen, Ben J.M, et al. “The conversion of (−)- and (+)-dihydrocarvone into chiral intermediates for the synthesis of (−)-polygodial, (−)-warburganal and (−)-muzigadial.” Tetrahedron, vol. 45, no. 5, Jan. 1989, pp. 1447-1452. https://doi.org/10.1016/0040-4020(89)80143-7.