Formal Synthesis of Angiopterlactone B via Enantioselective Reduction of Ketone with Daucus Carota Root

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.

Green synthesis of enantiopure quinoxaline alcohols using Daucus carota

“…[12][13][14] Sometimes, these biocatalyst reactions offer new synthetic opportunities in synthesis of chiral compounds which are otherwise difficult to obtain through traditional chemical catalytic transformations. [19][20][21] Immobilization of biocatalyst is emerging as a robust alternative process in up-scaling the biotransformation reactions and has several advantages such as easy separation, repeated use of biocatalyst for continuous-flow system and ease of the purification procedures. [15][16][17][18] Daucus carota is well known for number of biotransformation reactions due to the presence of alcohol dehydrogenase enzymes that are responsible for selective bioreduction of keto compounds.…”

“…[15][16][17][18] Daucus carota is well known for number of biotransformation reactions due to the presence of alcohol dehydrogenase enzymes that are responsible for selective bioreduction of keto compounds. [19][20][21] Immobilization of biocatalyst is emerging as a robust alternative process in up-scaling the biotransformation reactions and has several advantages such as easy separation, repeated use of biocatalyst for continuous-flow system and ease of the purification procedures. 22 Naoshima et al [23][24][25] applied immobilized cells of D carota for the bioreduction of several ketones to produce (S)-1-phenylethanol, (S)-1phenylpropanol, (S)-1-(naphthalene-1-yl)-ethanol in good yield and enantiomeric excess (ee).…”

Stereoselective Reducing Complexes Supported in Solid Phase: Preparation and Reactivity Study

“…Nowadays one of the most important challenges in organic chemistry is the preparation of new chiral molecules in enantiomerically pure forms, evaluating different ways to carry out the hydrogenation of prochiral molecules and better yet to obtain materials which can be a potential chiral catalyst . Multiple results about the synthesis of new enantiomerically pure materials that provides satisfactory results, and show high yields and enantioselectivity, have been reported. One disadvantage of the homogeneous synthesis is the difficulty to isolate the obtained product, since it is necessary to use chromatographic columns, extractions with different solvents or using specialized equipment such as HPLC.…”