Recent Advances in Total Synthesis of Prenylated Indole Alkaloids by Transition Metal-Catalyzed Reactions as the Key Step DOI Open Access

Tianfeng Peng,

Yuxiang Zhao,

Shaojian Pu

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(4), С. 1160 - 1160

Опубликована: Янв. 1, 2024

The prenylated indole alkaloids are an intriguning and important class of natural products encompassing ring, or derivatives thereof (that is, spirooxindole pseudoindowoxyl), decorated by one more prenyl groups the vestige a group.They comprise large structurally diverse family that display range biological properties.Nature employs dimethylallyl pyrophosphate (DMAPP) isopentenyl (IPP) as starting materials for biosynthesis numerous alkaloids.The core in these compounds is typically derived from L-tryptophan, less commonly indole-3-glycerol phosphate.Prenylation ubiquitous process common to almost all living organisms, key transformation organic synthesis.In recent years, have constantly received intensive research synthetic chemical community pharmacologists due their intriguing structural motifs profiles.To date, development straightforward efficient protocols enable synthesis highly desirable challenging.The advances total transition metal-catalyzed reactions step summarized.

Язык: Английский

Unified construction of prenylated and reverse-prenylated oxindoles from isoprene launched by Ni catalysis DOI
Yingying Liu, Ying Li, Xue-Ting Li

и другие.

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Год журнала: 2025, Номер 70, С. 444 - 454

Опубликована: Март 1, 2025

Язык: Английский

Процитировано

0
Asymmetric Synthesis of 10-Demethoxyvincorine Enabled by Dual Ni/Ti-Catalyzed Reductive Cyclization DOI

Yanxia Zhen,

Wei Jiang, Yuanzhen Xu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

Herein, we report the asymmetric synthesis of 10-demethoxyvincorine in 12 steps. The is highlighted by several key transformations: (1) a Pd-catalyzed Catellani-type reaction for preparation C2-alkylated tryptamine, (2) chiral phosphoric acid (CPA)-catalyzed bromocyclization to construct enantioenriched 3a-bromo-hexahydropyrroloindoline, (3) dual Ni/Ti-catalyzed reductive cyclization establish bridged ring system, and (4) SmI2-promoted forge strained E-ring.

Язык: Английский

Процитировано

0
Assembly of 3-Halooxindoles via Interrupted Semipinacol Rearrangement: Enabling Concise Total Synthesis of CPC-1 DOI
Yaoyao Liu, Yating Zhang,

Fan Zhang

и другие.

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134672 - 134672

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0
Catalytic Asymmetric Synthesis of Vicinal Quaternary Stereocenters Enabled by Alkylation of α,α-Disubstituted Aldehydes with 3-Bromooxindoles DOI
Longjun Dong, Qi Wang, Jingfeng Zhang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3086 - 3090

Опубликована: Апрель 9, 2024

An organocatalytic enantioselective alkylation of α,α-disubstituted aldehydes with 3-bromooxindoles is reported. Enantioenriched oxindoles vicinal quaternary stereocenters are accessed by an asymmetric conjugate addition process branched o-azaxylylene intermediates (indol-2-ones). Key to the success highly diastereo- and transformations combined use a triphenylsilyl-protected β-amino alcohol catalyst derived from spiropyrrolidine scaffold 3,5-dinitrobenzoic acid. This study also presents rare example aldehyde formation consecutive stereocenters.

Язык: Английский

Процитировано

2
Recent Advances in Total Synthesis of Prenylated Indole Alkaloids by Transition Metal-Catalyzed Reactions as the Key Step DOI Open Access

Tianfeng Peng,

Yuxiang Zhao,

Shaojian Pu

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(4), С. 1160 - 1160

Опубликована: Янв. 1, 2024

The prenylated indole alkaloids are an intriguning and important class of natural products encompassing ring, or derivatives thereof (that is, spirooxindole pseudoindowoxyl), decorated by one more prenyl groups the vestige a group.They comprise large structurally diverse family that display range biological properties.Nature employs dimethylallyl pyrophosphate (DMAPP) isopentenyl (IPP) as starting materials for biosynthesis numerous alkaloids.The core in these compounds is typically derived from L-tryptophan, less commonly indole-3-glycerol phosphate.Prenylation ubiquitous process common to almost all living organisms, key transformation organic synthesis.In recent years, have constantly received intensive research synthetic chemical community pharmacologists due their intriguing structural motifs profiles.To date, development straightforward efficient protocols enable synthesis highly desirable challenging.The advances total transition metal-catalyzed reactions step summarized.

Язык: Английский

Процитировано

0