The stereoselective total syntheses of pectinolides A, B, and C

被引：4

作者：

Ramulu, Udugu ^{[1
]}

Ramesh, Dasari ^{[1
]}

Reddy, Sudina Purushotham ^{[1
]}

Rajaram, Singanaboina ^{[1
]}

Babu, Katragadda Suresh ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 20-21期

关键词：

ACID-CATALYZED BENZYLATION; OXIDATION; LACTONES; ESTERS;

D O I：

10.1016/j.tetasy.2014.09.009

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective total synthesis of pectinolide B has been accomplished for the first time along with total syntheses of pectinolides A and C. MacMillan alpha-hydroxylation and Sharpless asymmetric dihydroxylation reactions are involved in generating the three stereogenic centers. Other important transformations in the synthesis are Z-selective Still-Gennari olefination, selective benzylation of the homoallylic alcohol, and a one-pot MOM deprotection followed by lactonization leading to all three pectinolides A-C being synthesized from a common intermediate. Pectinolides A, B, and C were synthesized from n-hexanal in 19, 20, and 18 steps with overall yields of 8.8%, 6.72%, and 9.2%, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1409 / 1417

页数：9

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