Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.
Publication
, Journal Article
Lanier, ML; Park, H; Mukherjee, P; Timmerman, JC; Ribeiro, AA; Widenhoefer, RA; Hong, J
Published in: Chemistry (Weinheim an der Bergstrasse, Germany)
May 2017
8-Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohols was explored to stereoselectively construct α,α'-cis-oxocenes and further applied in a formal synthesis of (+)-laurencin. The gold(I)-catalyzed intramolecular dehydrative alkoxylation may constitute an alternative method for the synthesis of molecular building blocks and natural products that contain highly functionalized 8-membered cyclic ethers.
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Published In
Chemistry (Weinheim an der Bergstrasse, Germany)
DOI
EISSN
1521-3765
ISSN
0947-6539
Publication Date
May 2017
Volume
23
Issue
30
Start / End Page
7180 / 7184
Related Subject Headings
- Stereoisomerism
- Propanols
- Oxocins
- Gold
- General Chemistry
- Ethers, Cyclic
- Catalysis
- Biological Products
- 34 Chemical sciences
- 03 Chemical Sciences
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Lanier, M. L., Park, H., Mukherjee, P., Timmerman, J. C., Ribeiro, A. A., Widenhoefer, R. A., & Hong, J. (2017). Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation. Chemistry (Weinheim an Der Bergstrasse, Germany), 23(30), 7180–7184. https://doi.org/10.1002/chem.201700499
Lanier, Megan L., Hyeri Park, Paramita Mukherjee, Jacob C. Timmerman, Anthony A. Ribeiro, Ross A. Widenhoefer, and Jiyong Hong. “Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.” Chemistry (Weinheim an Der Bergstrasse, Germany) 23, no. 30 (May 2017): 7180–84. https://doi.org/10.1002/chem.201700499.
Lanier ML, Park H, Mukherjee P, Timmerman JC, Ribeiro AA, Widenhoefer RA, et al. Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation. Chemistry (Weinheim an der Bergstrasse, Germany). 2017 May;23(30):7180–4.
Lanier, Megan L., et al. “Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.” Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 23, no. 30, May 2017, pp. 7180–84. Epmc, doi:10.1002/chem.201700499.
Lanier ML, Park H, Mukherjee P, Timmerman JC, Ribeiro AA, Widenhoefer RA, Hong J. Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation. Chemistry (Weinheim an der Bergstrasse, Germany). 2017 May;23(30):7180–7184.
Published In
Chemistry (Weinheim an der Bergstrasse, Germany)
DOI
EISSN
1521-3765
ISSN
0947-6539
Publication Date
May 2017
Volume
23
Issue
30
Start / End Page
7180 / 7184
Related Subject Headings
- Stereoisomerism
- Propanols
- Oxocins
- Gold
- General Chemistry
- Ethers, Cyclic
- Catalysis
- Biological Products
- 34 Chemical sciences
- 03 Chemical Sciences