182486-10-8Relevant articles and documents
Continuous Flow Synthesis of Terminal Epoxides from Ketones Using in Situ Generated Bromomethyl Lithium
Von Keutz, Timo,Cantillo, David,Kappe, C. Oliver
, p. 10094 - 10098 (2019)
A scalable procedure for the direct preparation of epoxides from ketones has been developed. The method is based on the carefully controlled generation of (bromomethyl)lithium (LiCH2Br) from inexpensive CH2Br2 and MeLi in a continuous flow reactor. The reaction has shown excellent selectivity for a variety of substrates, including α-chloroketones, which typically fail under classic Corey-Chaykovsky conditions. This advantage has been used to develop a novel route toward the drug fluconazole.
Chemoselective cross metathesis of bishomoallylic alcohols: Rapid access to fragment A of the cryptophycins
Lautens, Mark,Maddess, Matthew L.
, p. 1883 - 1886 (2007/10/03)
Equation presented. The racemic or enantioselective allylation of in situ formed β,γ-unsaturated aldehydes provides efficient access to bishomoallylic alcohols from readily available 2-vinyloxiranes. These products, when subjected to modified Grubbs cross
Total synthesis of cryptophycins via a chemoenzymatic approach
Salamonczyk, Grzegorz M.,Han, Kang,Guo, Zhi-Wei,Sih, Charles J.
, p. 6893 - 6900 (2007/10/03)
A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.
