Total synthesis, biological evaluation of dendrodolides A-D and their analogues

被引：7

作者：

Poornima, B. ^{[1
]}

Venkanna, A. ^{[1
]}

Swetha, B. ^{[2
]}

Kamireddy, Karthik Reddy ^{[2
]}

Siva, Bandi ^{[1
]}

Babu, V. S. Phani ^{[3
]}

Ummanni, Ramesh ^{[2
]}

Babu, K. Suresh ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, Ctr Chem Biol, Hyderabad 500007, Andhra Pradesh, India

[3] CSIR Indian Inst Chem Technol, Ctr NMR & Struct Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2016年 / 72卷 / 32期

关键词：

Macrolides; Yamaguchi esterification; RCM approach; Jacobsen hydrolytic kinetic resolution; Analogues; Cytotoxic activity; SAR studies; STEREOSELECTIVE TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; HYDROLYTIC KINETIC RESOLUTION; RING-CLOSING METATHESIS; FORMAL TOTAL-SYNTHESIS; ABSOLUTE-CONFIGURATION; COLORIMETRIC ASSAY; SWINHOLIDE-A; METABOLITES; MACROLIDES;

D O I：

10.1016/j.tet.2016.06.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise total synthesis of dendrodolides A-D (1-4) has been accomplished in 10 steps from commercially available (R)-propylene oxide and 3-buten-1-ol as starting materials. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification and ring-closing metathesis (RCM). In addition, a series of ester derivatives were prepared utilizing Yamaguchi esterification at the C-3 position of the dendrodolide core and screened for their efficacy against cancer cell lines. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：4789 / 4797

页数：9

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