Stereoselective Approach towards the Synthesis of 3R, 5 S Gingerdiol and 3 S, 5 S Gingerdiol

被引：6

作者：

Markad, Sachin B. ^{[1
]}

Bhosale, Viraj A. ^{[1
]}

Bokale, Suvarna R. ^{[1
]}

Waghmode, Suresh B. ^{[1
]}

机构：

[1] Savitribai Phule Pune Univ, Dept Chem, Pune 411007, Maharashtra, India

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 02期

关键词：

Asymmetric alpha-aminoxylation; gingerol; gingerdiols; HWE olefination; Wittig olefination; ASYMMETRIC ALPHA-AMINOXYLATION; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ALDEHYDES; AMINOOXYLATION; OLEFINATION; DERIVATIVES; PRINCIPLES; 1,2-DIOLS; ALCOHOLS; ANALOGS;

D O I：

10.1002/slct.201803154

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An operationally simple and concise stereoselective synthesis of both natural 3R, 5 S gingerdiol and 3 S, 5 S gingerdiol has been achieved from achiral n-heptanal by employing iterative proline catalysed alpha-aminoxylation, followed by Horner-Wadsworth-Emmons or Wittig olefination reactions as key steps. The adducts formed in high enantiopurity as well as syn or anti-1,3-diols units were synthesized with excellent diastereoselectivity from gamma-hydroxy aldehyde by using D or L- proline.

引用

页码：502 / 505

页数：4

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