Journal
ORGANIC LETTERS
Volume 23, Issue 3, Pages 920-924Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04125
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Funding
- National Natural Science Foundation of China [21672184, 21861042, 21801221]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT17R94]
- Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province
- Yunnan Province Government [2018FY001(016), YNQRQNRC-2018-005, 2019FD126]
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The study demonstrated that alpha-aryl cyclic vinylogous esters are effective substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, allowing for the straightforward enantioselective synthesis of common motifs found in various natural products. As an initial application of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (-)-mesembrine have been successfully completed in a divergent manner.
We demonstrate that alpha-aryl cyclic vinylogous esters are competent substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, enabling a straightforward enantioselective synthesis of 6-allyl-6-aryl-3-ethoxycyclohex-2-en-1-ones, common motifs embedded in numerous structurally diverse natural products. As an initial demonstration of the utility of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (-)-mesembrine have been completed divergently.
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