Ring-closing metathesis based total synthesis of ciliatamides A and B and their structural confirmation

被引：5
作者：
Avula, Krishnakumari [1 ]
Mohapatra, Debendra K. [1 ]
机构：
[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 15期
关键词：
Ciliatamides; Antileishmanial activity; Caprolactam; Amide bond formation; Ring-closing metathesis; 1ST TOTAL-SYNTHESIS; AMINO-ACIDS; MARINE SPONGE; A-C; STEREOCHEMISTRY; RCM;
D O I：
10.1016/j.tetlet.2016.03.017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Protecting group dependant ring-closing metathesis based approach to the total synthesis of the revised structures of ciliatamides A and B has been described. The current synthetic strategy utilizes the amino acid as starting material to introduce both the stereogenic centers. However, usage of non-racemizing reagents (EDC center dot HCI, HATU/NMM); for amide coupling and Grubbs' second generation catalyst for caprolactam ring synthesis makes the present approach more convenient to get the correct conclusion on absolute stereochemistry. Thus, on the basis of similar optical rotation values with the Lindsley's reported data, this synthesis further supported for the actual stereochemistry of both ciliatamides A and B is (R,R). (C) 2016 Elsevier Ltd. All rights reserved.
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收藏
页码：1715 / 1717
页数：3
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