Stereodivergent Total Synthesis of Hapalindoles, Fischerindoles, Hapalonamide H, and Ambiguine H Alkaloids by Developing a Biomimetic, Redox-Neutral, Cascade Prins-Type Cyclization

被引：21

作者：

Sahu, Samrat ^{[1
]}

Das, Beauty ^{[1
]}

Maji, Modhu Sudan ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 20期

关键词：

HAPALOSIPHON-FONTINALIS; FISCHERELLA-MUSCICOLA; PROTECTING GROUPS; NATURAL-PRODUCTS; CRUDE EXTRACT; CYANOBACTERIUM; ISONITRILE; INDOLES; WELWITINDOLINONES; ALLYLBORATION;

D O I：

10.1021/acs.orglett.8b02804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective, redox-neutral, Bronsted acid-catalyzed cascade Prins-type cyclization between indole and aldehyde is described to access several structurally diverse indole terpenoid scaffolds in a single step. Applying this concept, stereodivergent total syntheses of nine hapalindole-type alkaloids are accomplished. Key transformations include allylation using geometrically isomeric allylboronic acid followed by a p-toluenesulfonic acid mediated deprotection-cyclization cascade.

引用

页码：6485 / 6489

页数：5

共 3 条

[1] Stereodivergent total synthesis of hapalindoles, fischerindoles, hapalonamide H, and ambiguine H alkaloids by developing a biomimetic, redox-neutral, cascade Prins-type cyclization
Sahu, Samrat
Das, Beauty
Maji, Modhu
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[2] Cascade Synthesis of 3-Alkylidene Dihydrobenzofuran Derivatives via Rhodium(III)-Catalyzed Redox-Neutral C-H Functionalization/Cyclization
Zhou, Zhi
Liu, Guixia
Chen, Yan
Lu, Xiyan
[J]. ORGANIC LETTERS, 2015, 17 (23) : 5874 - 5877
[3] Redox-Neutral Photocatalytic Radical Cascade Cyclization for the Synthesis of CH2CN/CF2COOEt/CF3-Containing Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-One Derivatives
Liu, Liang
Yang, De-Yong
He, Yan-Hong
Guan, Zhi
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11892 - 11901

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