E. J. Corey's 1964 total synthesis of a-caryophyllene (essence of cloves) solves a number of problems of construction of unusual-sized rings. H H a-Caryophyllene The first step uses an efficient photochemical [2 + 2] reaction. The desired stereochem- istry and regiochemistry had been predicted based on model reactions. H (racemic) hv The next steps are shown here. H H 1. H,/Pd 2. CrO,/HOAC (A) -COOME -COOME (MeO),CH H Li

E. J. Corey's 1964 total synthesis of a-caryophyllene (essence of cloves) solves a number of problems of construction of unusual-sized rings. H H a-Caryophyllene The first step uses an efficient photochemical [2 + 2] reaction. The desired stereochem- istry and regiochemistry had been predicted based on model reactions. H (racemic) hv The next steps are shown here. H H 1. H,/Pd 2. CrO,/HOAC (A) -COOME -COOME (MeO),CH H Li

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.24P: The following equation shows the reaction of trans-2,3-diphenyloxirane with hydrogen chloride in...

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