Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization to Form a Medium-Sized Ring.

ChemInform ◽  
2006 ◽  
Vol 37 (15) ◽  
Author(s):  
Isamu Shiina ◽  
Minako Hashizume ◽  
Yu-suke Yamai ◽  
Hiromi Oshiumi ◽  
Takahisa Shimazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Enantioselective Total Synthesis

Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium-Sized Ring

2005 ◽  
Vol 11 (22) ◽  
pp. 6601-6608 ◽  
Author(s):  
Isamu Shiina ◽  
Minako Hashizume ◽  
Yu-suke Yamai ◽  
Hiromi Oshiumi ◽  
Takahisa Shimazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Enantioselective Total Synthesis

scholarly journals Application of sequential proline-catalyzed α-chlorination and aldol reactions in the total synthesis of 1-deoxygalactonojirimycin

2018 ◽  
Vol 96 (2) ◽  
pp. 144-147 ◽  
Author(s):  
Michael Meanwell ◽  
Mathew Sutherland ◽  
Robert Britton
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Single Step ◽  
Carbon Skeleton ◽  
Aldol Reactions ◽  
Protecting Group ◽  
One Pot ◽  
Enantioselective Total Synthesis ◽  
Epoxide Opening ◽  
Structural Analogues

A short enantioselective total synthesis of 1-deoxygalactonojirimycin (migalastat) has been achieved that does not rely on chiral pool starting materials or biocatalysis. Instead, this synthesis exploits a one-pot proline-catalyzed α-chlorination and aldol reaction of a commercially available aldehyde to assemble the entire carbon skeleton in a single step. The key role played by a nitrogen protecting group in the final epoxide opening reaction is highlighted as is the amenability to access structural analogues using this route.

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