Synthetic studies towards the formal synthesis of (+)-Neopeltolide
Ho, Iek Va
Date of Issue2010
School of Physical and Mathematical Sciences
A formal synthesis of (+)-Neopeltolide macrolactone system has been performed in a total of 14 steps with an overall yield of 6.3 %. The key steps include: 1. catalytic enantioselective copper-catalyzed 1, 4-conjugate addition of a methyl Grignard reagent to an a,(3-unsaturated ester in 95% d.e. and 35% yield ; 2. Indium-mediated Prins cyclization reaction between an aldehyde and a homoallylic alcohol to install the 2,4,6-trisubstituted tetrahydropyran moiety in 56% yield ; 3. A novel functional group conversion from an aliphatic dihalo to a ketone in 50% yield .
Nanyang Technological University