Stereospecific synthesis of dl-Cyclopenin (cas 19553-26-5) and dl-cyclopenol

Add time:08/23/2019    Source:sciencedirect.com

A stereospecific synthesis of dl-cyclopenin (1) is described corroborating previous structural and stereochemical assignments. The hippuric acid 10 was converted to cis ester 11 which was reduced and cyclized separately to cis and trans 3-benzylidene-4-methyl-1-H-1,4-benzodiazepin-2,5-diones 12 and 14. In an alternative approach, hippuric acid 5 was converted via oxazolone 4 to trans ester 9. Epoxidation of 14 gave 1. Extension of this scheme provided a synthetic route to dl-cyclopenol (2) via 10 → 19 → 23 → 23 → 26 → 2.

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