The journey of total synthesis toward nannocystin Ax

被引：8

作者：

Liu, Rong ^{[1
]}

Xia, Mengwei ^{[1
]}

Zhang, Yanhui ^{[1
]}

Fu, Shaomin ^{[1
]}

Liu, Bo ^{[1
,2
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China

[2] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China

来源：

TETRAHEDRON | 2019年 / 75卷 / 12期

关键词：

Nannocystin Ax; Total synthesis; Polyketide; Peptide; Stille coupling; ASYMMETRIC TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; ACID; ALDOL; EPOXIDATION; ANTICANCER; DERIVATIVES; VANCOMYCIN;

D O I：

10.1016/j.tet.2018.12.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe the detail on our full investigations that led to the achievement of the total synthesis of nannocystin Ax, a 21-membered macrocyclic natural product composing of a tripeptide fragment and a polyketide fragment, which featured in 8 longest linear steps in with 13.9% total overall yield. The key synthetic strategy relied on the late-stage stille coupling for the macrolactonization to construct the 21-membered ring, while direct connection between the tripeptide fragment and the polyketide fragment failed. H-1 NMR experiments reveal that nannocystin Ax should exist as conformational mixtures in deuterated solvents. (C) 2018 Elsevier Ltd. All rights reserved.

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页码：1781 / 1794

页数：14

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