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Open AccessArticle

A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs

Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road No. 95, Zhengzhou 450002, China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, School of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 57115, China
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, China
School of Sciences, China Agricultural University, Beijing 100193, China
Authors to whom correspondence should be addressed.
Academic Editor: Rafael Chinchilla
Molecules 2017, 22(3), 364;
Received: 18 January 2017 / Revised: 21 February 2017 / Accepted: 24 February 2017 / Published: 27 February 2017
(This article belongs to the Special Issue Asymmetric Synthesis 2017)
An efficient and practical synthetic route toward chiral matsutakeol and analogs was developed by asymmetric addition of terminal alkyne to aldehydes. (R)-matsutakeol and other flavored substances were feasibly synthesized from various alkylaldehydes in high yield (up to 49.5%, in three steps) and excellent enantiomeric excess (up to >99%). The protocols may serve as an alternative asymmetric synthetic method for active small-molecule library of natural fatty acid metabolites and analogs. These chiral allyl alcohols are prepared for food analysis and screening insect attractants. View Full-Text
Keywords: (R)-matsutakeol; general method; asymmetric catalysis; mushrooms; flavored analogs (R)-matsutakeol; general method; asymmetric catalysis; mushrooms; flavored analogs
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MDPI and ACS Style

Liu, J.; Li, H.; Zheng, C.; Lu, S.; Guo, X.; Yin, X.; Na, R.; Yu, B.; Wang, M. A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs. Molecules 2017, 22, 364.

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