First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening

被引：10

作者：

Ramesh, Perla ^{[1
]}

Reddy, Yarram Narasimha ^{[1
,2
]}

Reddy, Thatikonda Narendar ^{[3
]}

Srinivasu, Navuluri ^{[2
]}

机构：

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

[2] VFSTR Univ, Dept Sci & Humanities, Guntur 522213, India

[3] Indian Inst Chem Technol, CSIR, Crop Protect Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 02期

关键词：

CATALYTIC ASYMMETRIC ALLYLATION; STEREOSELECTIVE TOTAL-SYNTHESIS; CHIRAL LEWIS-ACID; BIS(((S)-BINAPHTHOXY)(ISOPROPOXY)TITANIUM) OXIDE; GONIOTHALAMUS-AMUYON; BIOSYNTHESIS; DERIVATIVES; METATHESIS; STYRYLLACTONES; REBECCAMYCIN;

D O I：

10.1016/j.tetasy.2017.01.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first protecting group-free total syntheses of the highly potent antitumor chlorinated styryllactone secondary metabolites 8-chlorogoniodiol, parvistone A, and one analogue 8-epi-parvistone A, have been accomplished from commercially available trans-cinnamaldehyde in five steps with high overall yields. The chlorine-bearing stereogenic center of these silent secondary metabolites was introduced via a bioinspired late-stage regioselective epoxide ring-opening strategy. Maruoka asymmetric allylation, acrylation, ring-closing metathesis and asymmetric epoxidation, greatly facilitate the synthesis of the key intermediates goniothalamin oxide and (6S,7S,8S)-isogoniothalamin oxide. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：246 / 249

页数：4