Attempts towards the synthesis of mupirocin-H

作者：Bommagani Shobanbabu^*; Thodupunuri Prashanth; Sharma Gangavaram V M

来源：ARKIVOC, 2017, 2017(4): 20-+.

DOI：10.24820/ark.5550190.p009.744

• Mupirocin-H
• Sharpless asymmetric epoxidation
• Wittig-olefination
• D-mannitol

The stereoselective synthesis of segments C1-C6 (3), C7-C12 (4) of mupirocin-H has been achieved. The synthetic procedure for the C1-C6 segment includes the zinc mediated ally! Grignard reaction with R-glyceraldehyde, Swern oxidation/Witting olefination reactions and followed by Sharpless asymmetric epoxidation. The C7-C12 segment was synthesized using again Sharpless asymmetric epoxidation on mono PMB protected 2-butene-1,4-diol, followed by regioselective opening of this epoxide with trimethyl aluminium. Both segments C1-C6 (3) and C7-C12 (4) possesses the five new stereogenic centers along with trans-olefin, but in various attempts condensation of 3 and 4 segments to give C-C bond forming parent segment (2) not affirmed, hence this work constitutes the synthesis of fragments C1-C6 (3) and C7-C12 (4) of mupirocin-H.
[GRAPHICS]
.

• 出版日期2017