期刊
TETRAHEDRON-ASYMMETRY
卷 18, 期 4, 页码 451-454出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2007.01.035
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The monoterpenoid pheromone (+)-eldanolide, a long range sex attractant, has been synthesized in four steps from the chiral 2,3-epoxy alcohol 4 in 36% overall yield. Our synthetic strategy features the formation of a 1,3-diol by regio- and stereoselective ring opening of 2,3-epoxy alcohol 4, an intermediate easily available from Sharpless asymmetric epoxidation. Other key steps include one carbon elongation, saponification, and lactonization. The present work constitutes a general method for the rapid synthesis of a number of related gamma-lactone natural products. (c) 2007 Elsevier Ltd. All rights reserved.
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