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

被引：5

作者：

Khomane, Navnath B. ^{[1
,2
]}

Patel, Javed S. ^{[1
,3
]}

Shirsat, Prashishkumar K. ^{[1
,2
]}

Mali, Prakash R. ^{[1
,2
]}

Meshram, Harshadas M. ^{[1
,2
]}

机构：

[1] Acad Sci & Innovat Res AcSIR, New Delhi, India

[2] Indian Inst Chem Technol, CSIR, Med Chem & Biotechnol Div, Hyderabad 500007, Andhra Pradesh, India

[3] Indian Inst Chem Technol, CSIR, Nat Product Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 05期

关键词：

Andos diaryl phosphonate; Daucus carota reduction; Hansen protocol; Hydrogenation; Mitsunobu inversion; Sharpless dihydroxylation;

D O I：

10.1002/slct.201703183

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-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.

引用

页码：1517 / 1520

页数：4

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