Formal Synthesis of Angiopterlactone B via Enantioselective Reduction of Ketone with Daucus Carota Root. Issue 5 (5th February 2018)

• Record Type: Journal Article
• Authors: Khomane, Navnath B.; Patel, Javed S.; Shirsat, Prashishkumar K.; Mali, Prakash R.; Meshram, Harshadas M.
• Is Part Of: ChemistrySelect. Volume 3:Issue 5(2018)
• Page Start: 1517
• Page End: 1520
• Publication Date: 2018-02-05
• Subjects: Andos diaryl phosphonate -- Daucus carota reduction -- Hansen protocol -- Hydrogenation -- Mitsunobu inversion -- Sharpless dihydroxylation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201703183
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Formal synthesis of angiopterlactone B has been accomplished via. enantioselective reduction of ketone with Daucus carota, Sharpless dihydroxylation and Andos modified Horner‐Wadsworth‐Emmons (HWE) reagent to introduce Z ‐olefination. Here we evolved a new path for the synthesis of ( S, S )‐osmundalactone and 3–5 dihydroxy γ‐caprolactone. The initial synthetic route for both caprolactone and osmundalcactone build on biocatalytic process while in later case Sharpless dihydroxylation delivered required stereocentres. Z ‐selective olefination was utilized to furnish caprolactone which was further recycled in to 1‐(5‐oxotetrahydrofuran‐2yl) ethyl 2‐phenyl acetate. Both synthetic routes found to be applicable for many synthetic reactions. Abstract : Formal synthesis of angiopterlactone B has been accomplished through the synthesis of ( S, S )‐osmundalactone and ( S, S )‐3‐5 dihydroxy γ‐caprolactone. The novelty of synthesis lies in Daucus carota reduction, Hansen semi‐reduction, Andos olefination, Mitsunobu inversion, Sharpless dihydroxylation