An efficient and economical approach to the synthesis of antitumor and anti‐inflammatory surinamensinol B (1) and antimalarial polysphorin analogue 2 has been achieved with high enantiomeric purity (96 % ee) by starting from commercially available 3,4,5‐trimethoxybenzaldehyde. The key steps of the strategy include a Co‐catalyzed two‐stereocentered hydrolytic kinetic resolution (HKR) of racemic 2‐[(methoxymethoxy)(3,4,5‐trimethoxyphenyl)methyl]oxirane (13) as the chiral inducing step followed by a Mitsunobu reaction. Chiral epoxide 14 and chiral diol 15 were utilized in the syntheses of both compounds.
A simple, organocatalytic procedure for the direct oxidative esterification of a variety of aromatic aldehydes with alcohols has been described that affords the corresponding aromatic esters in high yields. The method employs N-heterocyclic carbenes as catalysts and molecular O 2 as an oxidant under ambient conditions.
(+)‐L‐733,060 (I) is obtained by an asymmetric synthesis in 6 steps with an overall yield of 32% (93% e.e.) and (+)‐T‐2328 (II) in 10 steps with 28% overall yield (93% e.e.).
The present protocol provides optically active pyrazolidine carboxylates with derivatizable functional groups in high yields with excellent enantio- and diastereoselectivities.
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