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Formal Synthesis of Angiopterlactone B via Enantioselective Reduction of Ketone with Daucus Carota Root
Author(s) -
Khomane Navnath B.,
Patel Javed S.,
Shirsat Prashishkumar K.,
Mali Prakash R.,
Meshram Harshadas M.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201703183
Subject(s) - daucus carota , enantioselective synthesis , ketone , dihydroxylation , chemistry , reagent , organic chemistry , stereochemistry , combinatorial chemistry , botany , catalysis , biology
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.