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.
Highlights
Many natural unsaturated alcohols 1–6 (Figure 1) are very important fatty acid metabolites derived from fungi [1] and plants [2]
It strategy toward the total synthesis of
In yields and with we developed a general method with two steps to obtain highly enantioselective allyl alcohol flavors
Summary
Many natural unsaturated alcohols 1–6 (Figure 1) are very important fatty acid metabolites derived from fungi [1] and plants [2]. These substances have been found in nutrient, pharmaceutical, and agricultural use, as their structural diversity and variety of biological activities. The chiral allyl alcohols 6a–c (Figure 1) are a class of important flavor substances and dietary supplements which are widely used in the food industry [3,4,5]. (R)-matsutakeol 6a and its analogs are widely used in insecticidal compositions as effective attractants for some harmful hematophagous insects [8,9]. The enantioselectivity and chiral configuration of the compounds directly determined biological activities such as smell and taste [10]
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