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

页码：2366 / 2369

页数：4

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