Synthesis and Determination of Absolute Configuration of α-Pyrones Isolated from Penicillium corylophilum

被引：16
|
作者：
Yadav, J. S. [1 ,2 ]
Ganganna, B. [1 ,2 ]
Dutta, Palash [1 ,2 ]
Singarapu, Kiran K. [3 ]
机构：
[1] CSIR, Indian Inst Chem Technol, Acad Sci & Innovat Res, Hyderabad 500007, Andhra Pradesh, India
[2] CSIR, Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India
[3] CSIR, Indian Inst Chem Technol, Ctr NMR & Struct Chem, Hyderabad 500007, Andhra Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 22期
关键词：
STEREOSELECTIVE TOTAL-SYNTHESIS; STEREOCHEMICAL ASSIGNMENT;
D O I：
10.1021/jo5015382
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first total synthesis of (S)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one, 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxyundecyl)-2H-pyran-2-one, and its unnatural 2R,4R-isomer starting from commercially available 1,8-octanediol is described. The synthesis led to the revision of the proposed structural assignment of the natural product as (R)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one. The key steps include chiral auxiliary mediated asymmetric acetate aldol reaction, dianion addition, and base mediated cyclization to form an alpha-pyrone ring.
引用
收藏
页码：10762 / 10771
页数：10
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