Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers
Abstract
:Introduction
Results and Discussion
Conclusions
Compound | ||||
1 | ent-1 | 20 | ent-20 | |
Synthetic product (this work) | -73 | |||
Reported data | -96 [1] -77 [18] | +31 [7] | -22 [1, wrong] +43 [4] +33.4 [8] | -31 [17] |
Compound | ||||
2 | ent-2 | 21 | ent-21 | |
Synthetic product (this work) | -24 | - | - | - |
Reported data | - | +38 [3] | +40[20] | - |
No. | 1 | 1 | 20 | 20 | 2 | ent-2 | 21 |
---|---|---|---|---|---|---|---|
this work* | [18] | [20]* | [18] | this work* | [3] | [20]* | |
1 | 140.1 | 140.3 | 139.7 | 140.0 | 126.1 | 126.5 | 126.7 |
2 | 126.8 | 127.0 | 128.5 | 128.5 | 153.2 | 153.2 | 153.0 |
3 | 126.2 | 126.4 | 126.3 | 126.5 | 113.4 | 113.8 | 112.8 |
4 | 134.5 | 134.6 | 134.5 | 134.6 | 135.1 | 135.1 | 135.7 |
5 | 128.8 | 129.0 | 128.7 | 128.9 | 123.0 | 123.1 | 120.8 |
6 | 140.0 | 140.3 | 139.9 | 140.2 | 141.3 | 141.3 | 141.3 |
7 | 43.8 | 44.1 | 43.6 | 43.8 | 43.0 | 43.2 | 43.3 |
8 | 21.1 | 21.3 | 23.3 | 23.3 | 19.1 | 19.2 | 16.4 |
9 | 30.8 | 31.0 | 28.7 | 28.9 | 27.1 | 27.2 | 28.8 |
10 | 32.5 | 32.6 | 31.1 | 31.2 | 26.5 | 26.7 | 26.5 |
11 | 31.9 | 32.1 | 32.5 | 32.7 | 33.1 | 33.2 | 30.9 |
12 | 17.3 | 17.5 | 17.6 | 17.8 | 19.6 | 19.7 | 17.3 |
13 | 21.5 | 21.6 | 21.4 | 21.5 | 21.0 | 21.1 | 20.5 |
14 | 22.3 | 22.3 | 19.7 | 22.5 | 22.1 | 22.2 | 21.2 |
15 | 21.3 | 21.3 | 21.2 | 21.2 | 21.1 | 21.3 | 21.1 |
Experimental
General
Preparation of [1ξ,2ξ,3R,6S]-2-allyl-6-isopropyl-3-methyl-1-(2-methylpropyl)cyclohexan-1-ol (4).
Preparation of [1ξ,6ξ,7R,10S]-10-isopropyl-3,7-dimethylbicyclo[4.4.0]dec-3-en-1-ol (3).
Preparation of (-)-calamenene (1) and [7S,10R]-2,5-dihydrocalamenene (6).
Preparation of [1ξ,6ξ,7S,10R]-6-hydroxy-7-isopropyl-4,10-dimethylbicyclo[4.4.0]dec-3-en-2-one (8).
Preparation of (-)-[7S,10R]-2-hydroxycalamenene (2).
Acknowledgements
References and Notes
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- Sample Availability: Samples are not available.
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Nakashima, K.; Imoto, M.; Sono, M.; Tori, M.; Nagashima, F.; Asakawa, Y. Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers. Molecules 2002, 7, 517-527. https://doi.org/10.3390/70700517
Nakashima K, Imoto M, Sono M, Tori M, Nagashima F, Asakawa Y. Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers. Molecules. 2002; 7(7):517-527. https://doi.org/10.3390/70700517
Chicago/Turabian StyleNakashima, Katsuyuki, Masashi Imoto, Masakazu Sono, Motoo Tori, Fumihiro Nagashima, and Yoshinori Asakawa. 2002. "Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers" Molecules 7, no. 7: 517-527. https://doi.org/10.3390/70700517