ChemInform Abstract: A Chemoenzymatic Elaboration of a Quaternary Chiral Center: An Alternative Approach to the Side Chain of Furaquinocin D.

✍ Scribed by T. AKEBOSHI; Y. OHTSUKA; T. SUGAI; H. OHTA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199839208

✦ Synopsis

A Chemoenzymatic Elaboration of a Quaternary Chiral Center: An Alternative Approach to the Side Chain of Furaquinocin D.

-In the synthesis of naturally occurring compounds containing a quaternary chiral center, such as furaquinocin D, the intermediates containing contiguous chiral centers, consisting of a quaternary chiral center and an adjacent sec. alcohol play important roles. Here a new short-step approach to chiral (IV) is described, a compound which is related to a synthetic intermediate (VI) of the side chain of furaquinocin D. The synthesis which starts from a commercially available ketoester (I), is based on the preparation of a diastereomerically defined rac. alcohol (II) by the preferential degradation of one diastereomer using excess NaBH 4 and the subsequent lipase-catalyzed kinetic resolution, which yields the desired product highly enantioselectively in a preparative scale.