Stereoselective Total Synthesis of Carolacton

被引：37
|
作者：
Kuilya, Tapan Kumar [1 ]
Goswami, Rajib Kumar [1 ]
机构：
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 09期
关键词：
BACTERIUM STREPTOCOCCUS-MUTANS; BINDING MACROLIDE RHIZOPODIN; ASYMMETRIC ALDOL ADDITIONS; RING-CLOSING METATHESIS; CLAISEN REARRANGEMENT; BIOFILM INHIBITOR; FORMAL SYNTHESIS; FRAGMENT; ENOLATE; CARIES;
D O I：
10.1021/acs.orglett.7b00903
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short and convergent strategy for the stereoselective total synthesis of biologically active natural product carolacton has been accomplished. Our synthesis highlights the Urpi acetal aldol; Crimmins aldol, Ireland-Claisen rearrangement, TiCl4-assisted aldol followed by beta-hydroxy elimination to construct C-7=C-8 olefin, and ring-closing metathesis as the key steps for achieving the target molecule with an overall yield of 18.8%.
引用
收藏
页码：2366 / 2369
页数：4
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