155645-51-5Relevant articles and documents
Frontiers and opportunities in chemoenzymatic synthesis
Mortison, Jonathan D.,Sherman, David H.
scheme or table, p. 7041 - 7051 (2010/12/20)
Natural product biosynthetic pathways have evolved enzymes with myriad activities that represent an expansive array of chemical transformations for constructing secondary metabolites. Recently, harnessing the biosynthetic potential of these enzymes through chemoenzymatic synthesis has provided a powerful tool that often rivals the most sophisticated methodologies in modern synthetic chemistry and provides new opportunities for accessing chemical diversity. Herein, we describe our research efforts with enzymes from a broad collection of biosynthetic systems, highlighting recent progress in this exciting field.
A convergent synthesis of (+)-cryptophycin B, a potent antitumor macrolide from Nostoc sp. cyanobacteria.
Ghosh,Bischoff
, p. 1573 - 1575 (2007/10/03)
[structure--see text] An efficient and highly stereoselective synthesis of cryptophycin B (2), a potent cytotoxic agent, is described. The ester-derived titanium-enolate-mediated syn-aldol reaction was employed to generate the stereocenters C(5) and C(6). The route is convergent and provides a convenient access to the synthesis of structural variants of cryptophycin B as well as members of its family.
Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae
White, James D.,Hong, Jian,Robarge, Lonnie A.
, p. 6206 - 6216 (2007/10/03)
A convergent synthesis of cryptophycins has been developed in which (5S,6R)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic acid (A) is coupled with an amino acid segment (B). Two stereo-selective routes to A are described, the first employing allylatio