Abstract
A concise and general strategy for the total synthesis of the phenanthroquinolizidine alkaloids has been developed. An iterative Suzuki-Miyaura coupling reaction between the requisite aryl boronic acid, 2-bromo-4,5-dimethoxyphenyl N-methyliminodiacetate (MIDA) boronate derived from boronic acid, and a suitable bromopyridine substrate bearing a homopropargyl alcohol at the 2-position generated the desired ortho-aza-terphenyl compounds. Hydrogenation of the triple bond followed by treatment with methanesulfonyl chloride afforded their corresponding tetrahydroquinolizinium ion intermediates, which were subsequently reacted with NaBH4 to provide the desired hexahydroquinolizine products. A final oxidative electrocyclization reaction gave the target phenanthroquinolizidine natural products. This synthetic approach only requires the use of three chromatographic separations throughout the entire synthesis.
| Original language | English |
|---|---|
| Pages (from-to) | 11902-11910 |
| Number of pages | 9 |
| Journal | The Journal of organic chemistry |
| Volume | 84 |
| Issue number | 18 |
| DOIs | |
| Publication status | Published - 2019 Sep 20 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Total Synthesis of Phenanthroquinolizidine Alkaloids Using a Building Block Strategy. / Jo, Young In; Cheon, Cheol-Hong.
In: The Journal of organic chemistry, Vol. 84, No. 18, 20.09.2019, p. 11902-11910.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total Synthesis of Phenanthroquinolizidine Alkaloids Using a Building Block Strategy
AU - Jo, Young In
AU - Cheon, Cheol-Hong
PY - 2019/9/20
Y1 - 2019/9/20
N2 - A concise and general strategy for the total synthesis of the phenanthroquinolizidine alkaloids has been developed. An iterative Suzuki-Miyaura coupling reaction between the requisite aryl boronic acid, 2-bromo-4,5-dimethoxyphenyl N-methyliminodiacetate (MIDA) boronate derived from boronic acid, and a suitable bromopyridine substrate bearing a homopropargyl alcohol at the 2-position generated the desired ortho-aza-terphenyl compounds. Hydrogenation of the triple bond followed by treatment with methanesulfonyl chloride afforded their corresponding tetrahydroquinolizinium ion intermediates, which were subsequently reacted with NaBH4 to provide the desired hexahydroquinolizine products. A final oxidative electrocyclization reaction gave the target phenanthroquinolizidine natural products. This synthetic approach only requires the use of three chromatographic separations throughout the entire synthesis.
AB - A concise and general strategy for the total synthesis of the phenanthroquinolizidine alkaloids has been developed. An iterative Suzuki-Miyaura coupling reaction between the requisite aryl boronic acid, 2-bromo-4,5-dimethoxyphenyl N-methyliminodiacetate (MIDA) boronate derived from boronic acid, and a suitable bromopyridine substrate bearing a homopropargyl alcohol at the 2-position generated the desired ortho-aza-terphenyl compounds. Hydrogenation of the triple bond followed by treatment with methanesulfonyl chloride afforded their corresponding tetrahydroquinolizinium ion intermediates, which were subsequently reacted with NaBH4 to provide the desired hexahydroquinolizine products. A final oxidative electrocyclization reaction gave the target phenanthroquinolizidine natural products. This synthetic approach only requires the use of three chromatographic separations throughout the entire synthesis.
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UR - http://www.scopus.com/inward/citedby.url?scp=85072509732&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b01768
DO - 10.1021/acs.joc.9b01768
M3 - Article
VL - 84
SP - 11902
EP - 11910
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 18
ER -