title: A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs.
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.
authors.affiliation: 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. ljia198346@163.com.
authors.forename: Jia
authors.initials: J
authors.lastname: Liu
authors.affiliation: 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. honglianli@sina.com.
authors.forename: Honglian
authors.initials: H
authors.lastname: Li
authors.affiliation: Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, School of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 57115, China. zhengchaoustc@163.com.
authors.forename: Chao
authors.initials: C
authors.lastname: Zheng
authors.affiliation: 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. 15517151076@163.com.
authors.forename: Shichao
authors.initials: S
authors.lastname: Lu
authors.affiliation: 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. guoxianru@126.com.
authors.forename: Xianru
authors.initials: X
authors.lastname: Guo
authors.affiliation: 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. xinmingyin@hotmail.com.
authors.forename: Xinming
authors.initials: X
authors.lastname: Yin
authors.affiliation: 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. nrs@henau.edu.cn.|School of Sciences, China Agricultural University, Beijing 100193, China. nrs@henau.edu.cn.
authors.forename: Risong
authors.initials: R
authors.lastname: Na
authors.affiliation: School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, China. risongna@163.com.
authors.forename: Bin
authors.initials: B
authors.lastname: Yu
authors.affiliation: School of Sciences, China Agricultural University, Beijing 100193, China. wangmincau@outlook.com.
authors.forename: Min
authors.initials: M
authors.lastname: Wang
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D020005:Propanols; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000480:Alkynes; D020005:Propanols; C006463:allyl alcohol
keywords: (R)-matsutakeol; asymmetric catalysis; flavored analogs; general method; mushrooms