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Molecules 2017, 22(3), 364; doi:10.3390/molecules22030364

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

1
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
2
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, School of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 57115, China
3
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, China
4
School of Sciences, China Agricultural University, Beijing 100193, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Rafael Chinchilla
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)
View Full-Text   |   Download PDF [1558 KB, uploaded 27 February 2017]   |  

Abstract

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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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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