Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 13, Pages 5506-5512Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2008324
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- Japan Society for the Promotion of Science (JSPS)
- Grants-in-Aid for Scientific Research [22590005, 22106521] Funding Source: KAKEN
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Asymmetric formal synthesis of (+)-lysergic acid was achieved with a reductive ring-opening reaction of chiral 2-alkynyl-3-indolyloxirane with NaBH3CN as the key step. With Zn(OTf)(2) as an additive, the ring-opening reaction proceeded regioselectively at the 3-position to give the corresponding propargyl alcohol, which was a precursor of the allenic amide for palladium-catalyzed domino cyclization to construct the ergot alkaloid core structure.
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