Corey-Fuchs homologation

Corey-Fuchs Dibromoolefination, Corey-Fuchs Homologation, Corey-Fuchs Olefination)... 

A key fragment of (—)-amphidinolide E is synthesized from TBDPS ether of methyl (5)-3-hydroxy-2-methylpropanoate through reduction, oxidation, Corey-Fuchs homologation, hydroboration-hydrolysis (utilizing DBBS), Suzuki coupling, deprotection, and oxidation (eq 26). ... 

Terminal alkenylstannanes can be prepared after homologation of aldehydes via the Corey-Fuchs reaction.95... 

The stereoselective synthesis of the C5-C20 subunit of the aplyronine family of polyketide marine macrolides was accomplished by J.A. Marshall and co-workers. The C15-C20 moiety was prepared using the original Seyferth-Gilbert homologation conditions. The diazophosphonate was deprotonated with potassium fert-butoxide at low temperature, and then the solution of the aldehyde was added slowly also at low temperature. Interestingly, the alternative Corey-Fuchs alkyne synthesis was unsuccessful on this substrate, since extensive decomposition was observed. 

Corey-Fuchs alkyne synthesis One-carbon homologation of aldehydes to form the corresponding terminal alkynes. 104... 

With a bountiful supply of 69 at our disposal, the synthesis was continued by PCC oxidation to the aldehyde level and application of the Corey-Fuchs procedure [35] for chain homologation via dibromo olefin 70 to the acetylenic ester 71. Since amide bond construction next had to be implemented, this ester was saponified under mild conditions and the resulting carboxylic acid was activated by formation of a mixed anhydride with mesitylenesulfonyl chloride in advance of in situ condensation with 59. In order to preclude hydrolysis of the silyl ether functionality in 72, deacetalization had to be performed under anhydrous conditions in dry acetone containing a catalytic quantity of p-toluene-... 

Amdt-Eistert homologation Baylis-Hillman reaction Benzoin condensation Corey-Fuchs reaction Henry reaction (Nitroaldol reaction)... 

Sol 3. (d) The first step involves Corey—Fuchs reaction One-carbon homologation of an aldehyde to dibromoolefin, which is then treated with n-BuLi to produce a terminal alkyne. 

Corey-Fuchs reaction is a two step reaction converting an aldehyde to an alkyne by one-carbon homologation of the aldehyde. The Wittig-like reaction of aldehyde 1 and dibromocarbene forms dibromoalkene 2. The treatment of dibromoalkene 2 with two equivalent of -BuLi form a lithium alkynylide, quenched by eletrophiles, such as proton, CO2, aldehydes, ketones, and alkyl halides to form alkyne 3. 

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