Synthesis of (+)-bovidic acid
Abstract
(+)-Bovidic acid is an 18-carbon hydroxyfuranoid acid isolated from the pelage of the gaur (Bos frontalis) and displays potential as an insect repellant. Both a formal and total synthesis of (+)-bovidic acid was carried out with the core of the natural product being synthesized through Mukaiyama aerobic oxidative cyclization employing the second-generation Co(nmp)2 catalyst.
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Two studies have found bovidic acid to have mosquito repellent properties.
“The oil, identified as 5-(1-hydroxynonyl)-2-tetrahydrofuranpentanoic acid, has been named bovidic acid (Ishii et al. 2004), and 2 studies have found it to have mosquito repellent properties (Tran and Chauhan 2007;Phillips et al. 2015).”
From Bos frontalis and Bos gaurus (Artiodactyla: Bovidae) (2018) · cites this paper as Phillips et al. 2015
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Bos frontalis and Bos gaurus (Artiodactyla: Bovidae)
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Gaur genome reveals expansion of sperm odorant receptors in domesticated cattle
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Additional file 2 of Gaur genome reveals expansion of sperm odorant receptors in domesticated cattle
Low, W. Y., Rosen, B. D., Ren, Y., Bickhart, D. M., To, T., Martin, F. J., Billis, K., Sonstegard, T. S., Sullivan, S. T., Hiendleder, S., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19711493
Additional file 1 of Gaur genome reveals expansion of sperm odorant receptors in domesticated cattle
Low, W. Y., Rosen, B. D., Ren, Y., Bickhart, D. M., To, T., Martin, F. J., Billis, K., Sonstegard, T. S., Sullivan, S. T., Hiendleder, S., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19711490
- Authors
- Phillips, G. A., Wright, T. B., Stevens, A. C., & Pagenkopf, B. L.
- Affiliations
- Western University (CA)
- Venue
- Canadian Journal of Chemistry
- Publisher
- Canadian Science Publishing
- Published
- 2015-02
- Volume
- 93
- Issue
- 2
- Pages
- 196-198
- ISSN
- 0008-4042 (ISSN-L)
- 1480-3291
- OpenAlex
- W1943155591
- Cited by
- 8
- References
- 18
- Citations by year
- 2022: 3 · 2020: 1 · 2018: 1 · 2016: 2 · 2015: 1
- FWCI
- 0.44
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Canadian Journal of Chemistry (publishedVersion)
- Scholarship@Western (Western University) (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Keywords
- total synthesis, insect repellents, cobalt catalysts, natural product synthesis
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