Biocatalytic Approach for the Total Synthesis of (–)‐Malyngolide and Its C(5)‐Epimer

Abstract

An enzymatic approach has been successfully utilized in the total synthesis of (-)-malyngolide and its C(5)-epimer. The required configuration was established by an enzymatic kinetic resolution and Sharpless asymmetric dihydroxylation. Results and DiscussionFollowing our interest in the total synthesis of natural products [7], we herein report an efficient synthetic route for the total synthesis of (-)-malyngolide (1a) and its epimer 1b. In our retrosynthetic analysis, we proposed Figure. Examples of d-lactone-containing natural products.

Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis

“…The optimal stereochemistry of the β-methyl group will be determined once again by the synthesis and evaluation of both diastereomers. A number of approaches to asymmetric synthesis of 2 have been published since the first report by Mukaiyama in 1980 [18], including the use of chiral auxiliary [19][20][21][22][23][24][25][26][27], chiral pool [28][29][30][31][32][33][34][35][36][37], other asymmetric syntheses [38][39][40] and catalytic asymmetric syntheses [41][42][43][44][45][46][47][48][49].…”