Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core.
Publication
, Journal Article
Craig, RA; Smith, RC; Roizen, JL; Jones, AC; Virgil, SC; Stoltz, BM
Published in: The Journal of organic chemistry
June 2019
Late-stage synthetic efforts to advance the enatio- and diastereoselectively constructed [6,7,5,5]-fused tetracyclic scaffold toward the polycyclic norditerpenoid ineleganolide are disclosed. The described investigations focus on oxidation-state manipulation around the central cycloheptane ring. Computational evaluation of ground-state energies of dihydroineleganolide is used to rationalize empirical observations and provide insight for further synthetic development, enhancing the understanding of the conformational constraints of these compact polycyclic structures. Advanced synthetic manipulations generated a series of natural product-like compounds termed the ineleganoloids.
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Published In
The Journal of organic chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
June 2019
Volume
84
Issue
12
Start / End Page
7722 / 7746
Related Subject Headings
- Stereoisomerism
- Polycyclic Compounds
- Oxidation-Reduction
- Organic Chemistry
- Lactones
- Furans
- Diterpenes
- Cyclization
- Chemistry Techniques, Synthetic
- 3405 Organic chemistry
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Craig, R. A., Smith, R. C., Roizen, J. L., Jones, A. C., Virgil, S. C., & Stoltz, B. M. (2019). Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core. The Journal of Organic Chemistry, 84(12), 7722–7746. https://doi.org/10.1021/acs.joc.9b00635
Craig, Robert A., Russell C. Smith, Jennifer L. Roizen, Amanda C. Jones, Scott C. Virgil, and Brian M. Stoltz. “Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core.” The Journal of Organic Chemistry 84, no. 12 (June 2019): 7722–46. https://doi.org/10.1021/acs.joc.9b00635.
Craig RA, Smith RC, Roizen JL, Jones AC, Virgil SC, Stoltz BM. Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core. The Journal of organic chemistry. 2019 Jun;84(12):7722–46.
Craig, Robert A., et al. “Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core.” The Journal of Organic Chemistry, vol. 84, no. 12, June 2019, pp. 7722–46. Epmc, doi:10.1021/acs.joc.9b00635.
Craig RA, Smith RC, Roizen JL, Jones AC, Virgil SC, Stoltz BM. Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core. The Journal of organic chemistry. 2019 Jun;84(12):7722–7746.
Published In
The Journal of organic chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
June 2019
Volume
84
Issue
12
Start / End Page
7722 / 7746
Related Subject Headings
- Stereoisomerism
- Polycyclic Compounds
- Oxidation-Reduction
- Organic Chemistry
- Lactones
- Furans
- Diterpenes
- Cyclization
- Chemistry Techniques, Synthetic
- 3405 Organic chemistry