Catalytic Asymmetric Total Synthesis of (−)-Garryine via an Enantioselective Heck Reaction
Chuang Li
1
,
Fei Lu
1
,
Yukun Cai
1
,
Cheng Zhang
1
,
Yu Shao
1
,
Yuanyuan Zhang
1
,
Xiao-Yu Liu
1
,
Yong Qin
1
Publication type: Journal Article
Publication date: 2023-12-19
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
38113465
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The first asymmetric total synthesis of the hexacyclic veatchine-type C20-diterpenoid alkaloid (−)-garryine is presented. Key steps include a Pd-catalyzed enantioselective Heck reaction, a radical cyclization, and a photoinduced C–H activation/oxazolidine formation sequence. Of note, a highly enantioselective Heck reaction developed in this work provides efficient access to 6/6/6 tricyclic compounds, in particular, containing a C19-functionalitiy, which is useful for diverse transformations.
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Citations from 2024:
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GOST
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Li C. et al. Catalytic Asymmetric Total Synthesis of (−)-Garryine via an Enantioselective Heck Reaction // Journal of the American Chemical Society. 2023. Vol. 146. No. 1. pp. 1081-1088.
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Li C., Lu F., Cai Y., Zhang C., Shao Yu., Zhang Y., Liu X., Qin Y. Catalytic Asymmetric Total Synthesis of (−)-Garryine via an Enantioselective Heck Reaction // Journal of the American Chemical Society. 2023. Vol. 146. No. 1. pp. 1081-1088.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jacs.3c12171
UR - https://pubs.acs.org/doi/10.1021/jacs.3c12171
TI - Catalytic Asymmetric Total Synthesis of (−)-Garryine via an Enantioselective Heck Reaction
T2 - Journal of the American Chemical Society
AU - Li, Chuang
AU - Lu, Fei
AU - Cai, Yukun
AU - Zhang, Cheng
AU - Shao, Yu
AU - Zhang, Yuanyuan
AU - Liu, Xiao-Yu
AU - Qin, Yong
PY - 2023
DA - 2023/12/19
PB - American Chemical Society (ACS)
SP - 1081-1088
IS - 1
VL - 146
PMID - 38113465
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (up to 50 authors)
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@article{2023_Li,
author = {Chuang Li and Fei Lu and Yukun Cai and Cheng Zhang and Yu Shao and Yuanyuan Zhang and Xiao-Yu Liu and Yong Qin},
title = {Catalytic Asymmetric Total Synthesis of (−)-Garryine via an Enantioselective Heck Reaction},
journal = {Journal of the American Chemical Society},
year = {2023},
volume = {146},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://pubs.acs.org/doi/10.1021/jacs.3c12171},
number = {1},
pages = {1081--1088},
doi = {10.1021/jacs.3c12171}
}
Cite this
MLA
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Li, Chuang, et al. “Catalytic Asymmetric Total Synthesis of (−)-Garryine via an Enantioselective Heck Reaction.” Journal of the American Chemical Society, vol. 146, no. 1, Dec. 2023, pp. 1081-1088. https://pubs.acs.org/doi/10.1021/jacs.3c12171.