An Efficient Synthesis of (+)-Subersic Acid
Jing Wang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorPeiqiang Wang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorJue Li
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorCorresponding Author
Peiying Wu
School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
Peiying Wu, School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203
Jiangmeng Ren, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Bubing Zeng, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Search for more papers by this authorCorresponding Author
Jiangmeng Ren
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Peiying Wu, School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203
Jiangmeng Ren, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Bubing Zeng, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Search for more papers by this authorCorresponding Author
Bubing Zeng
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Peiying Wu, School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203
Jiangmeng Ren, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Bubing Zeng, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Search for more papers by this authorJing Wang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorPeiqiang Wang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorJue Li
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorCorresponding Author
Peiying Wu
School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
Peiying Wu, School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203
Jiangmeng Ren, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Bubing Zeng, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Search for more papers by this authorCorresponding Author
Jiangmeng Ren
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Peiying Wu, School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203
Jiangmeng Ren, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Bubing Zeng, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Search for more papers by this authorCorresponding Author
Bubing Zeng
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Peiying Wu, School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203
Jiangmeng Ren, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Bubing Zeng, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China, Tel.: 0086-021-64253689
Search for more papers by this authorAbstract
This paper describes a concise and practical route to (+)-subersic acid from naturally occurring (−)-Sclareol in 7 steps. The key step of this route relied on the cross coupling of the diterpene with the arene fragment using the arylation of allylic acetate followed by β-acetoxy elimination type Heck reaction.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| cjoc_201500219_sm_suppl.pdf102.3 KB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1 Carroll, J.; Jonsson, E. N.; Ebel, R.; Hartman, M. S.; Holman, T. R.; Crews, P.. J. Org. Chem., 2001, 66, 6847.
- 2
Tanada, Y.;
Mori, K..
Eur. J. Org. Chem.,
2003,
5,
848.
10.1002/ejoc.200390128 Google Scholar
- 3 Basabe, P.; Diego, A.; Delgado, S.; Diez, D.; Marcos, I. S.; Urones, J. G.. Tetrahedron, 2003, 59, 9173.
- 4 Williams, D. E.; Telliez, J. B.; Liu, J.; Tahir, A.; Van Soest, B.; Andersen, R. J.. J. Nat. Prod., 2004, 67, 2127.
- 5 Hua, S. K.; Wang, J.; Chen, X. B.; Xu, Z. Y.; Zeng, B. B.. Tetrahedron, 2011, 67, 1142.
- 6a Liu, Y.; Yao, B.; Deng, C. L.; Tang, R. Y.; Zhang, X. G.; Li, J. H.. Org. Lett., 2011, 13, 1126.
- 6b Le, B. J.; Muzart, J.. Tetrahedron, 2012, 68, 10065.
- 6c Lautens, M.; Tayama, E.; Herse, C.. J. Am. Chem. Soc., 2005, 127, 72.
- 6d Seomoon, D.; Lee, K.; Kim, H.; Lee, P. H.. Chem. Eur. J., 2007, 13, 5197.
- 7 Chakraborti, A. K.; Sharma, L.; Nayak, M. K.. J. Org. Chem., 2002, 67, 6406.
Citing Literature
