Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization

2017 ◽  
Vol 56 (42) ◽  
pp. 12888-12891 ◽  
Author(s):  
Anna Sib ◽  
Tobias A. M. Gulder
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Oxidative Dearomatization

Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy Inspired by Chemical Network Analysis

2019 ◽  
Author(s):  
Kyle Owens ◽  
Shelby McCowen ◽  
Katherine Blackford ◽  
Sohei Ueno ◽  
Yasuo Hirooka ◽  
...  
Keyword(s):  
Natural Products ◽  
Network Analysis ◽  
Total Synthesis ◽  
Ring System ◽  
Diels Alder ◽  
Diterpenoid Alkaloids ◽  
Oxidative Dearomatization ◽  
Diterpenoid Alkaloid ◽  
Fused Ring ◽  
Fused Ring System

Arcutinidine and other arcutinidine-type diterpenoid alkaloids feature an intricate polycyclic, bridged framework with unusual connectivity. A chemical network analysis approach to the arcutane skeleton enabled the identification of highly simplifying retrosynthetic disconnections, which indicated that the caged structure could arise from a simpler fused ring system. On this basis, a total synthesis of arcutinidine is reported herein, featuring an unprecedented oxopyrrolium Diels–Alder cycloaddition which furnishes a key tetracyclic intermediate. In addition, the synthesis utilizes a diastereoselective oxidative dearomatization/cycloaddition sequence and a SmI2-mediated C–C coupling to forge the bridged framework of the natural products. This synthetic plan may also enable future investigations into the biosynthetic relationships between the arcutanes, the related diterpenoid atropurpuran, and other diterpenoid alkaloids.

Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy Inspired by Chemical Network Analysis

2019 ◽  
Author(s):  
Kyle Owens ◽  
Shelby McCowen ◽  
Katherine Blackford ◽  
Sohei Ueno ◽  
Yasuo Hirooka ◽  
...  
Keyword(s):  
Natural Products ◽  
Network Analysis ◽  
Total Synthesis ◽  
Ring System ◽  
Diels Alder ◽  
Diterpenoid Alkaloids ◽  
Oxidative Dearomatization ◽  
Diterpenoid Alkaloid ◽  
Fused Ring ◽  
Fused Ring System

Arcutinidine and other arcutinidine-type diterpenoid alkaloids feature an intricate polycyclic, bridged framework with unusual connectivity. A chemical network analysis approach to the arcutane skeleton enabled the identification of highly simplifying retrosynthetic disconnections, which indicated that the caged structure could arise from a simpler fused ring system. On this basis, a total synthesis of arcutinidine is reported herein, featuring an unprecedented oxopyrrolium Diels–Alder cycloaddition which furnishes a key tetracyclic intermediate. In addition, the synthesis utilizes a diastereoselective oxidative dearomatization/cycloaddition sequence and a SmI2-mediated C–C coupling to forge the bridged framework of the natural products. This synthetic plan may also enable future investigations into the biosynthetic relationships between the arcutanes, the related diterpenoid atropurpuran, and other diterpenoid alkaloids.

Application of Dess-Martin oxidation in total synthesis of natural products

2020 ◽  
Vol 17 ◽  
Author(s):  
Majid M. Heravi ◽  
Tayebe Momeni ◽  
Vahideh Zadsirjan ◽  
Leila Mohammadi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Selective Oxidation ◽  
Secondary Alcohols ◽  
Aldehydes And Ketones

: Dess–Martin periodinane (DMP), is a commercially available chemical, frequently being utilized as a mild oxidative agent for the selective oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively. DMP shows several merits over other common oxidative agent such as chromium- and DMSO-based oxidants, thus it is habitually employed in the total synthesis of natural products. In this review, we try to underscore the applications of DMP as an effective oxidant in an appropriate step (steps) in the multistep total synthesis of natural products.

scholarly journals Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 720
Author(s):  
Satomi Niwayama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Organic Compounds ◽  
Recent Progress ◽  
Aqueous Media ◽  
Building Blocks ◽  
Organic Reactions ◽  
Environmentally Benign ◽  
Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

Total synthesis: the structural confirmation of natural products

2021 ◽  
Vol 57 (27) ◽  
pp. 3307-3322
Author(s):  
Debobrata Paul ◽  
Ashis Kundu ◽  
Sanu Saha ◽  
Rajib Kumar Goswami
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Feature Article

This feature article highlights total synthesis as one of the reliable tools for the structural confirmation of natural products.

Unified enantioselective total synthesis of 3,6-dioxygenated diketopiperazine natural products, diatretol and lepistamides A, B and C

2021 ◽  
Vol 67 ◽  
pp. 152895
Author(s):  
Shu Takahashi ◽  
Aoi Kimishima ◽  
Tomoyasu Hirose ◽  
Takeshi Yamada ◽  
Akihiro Sugawara ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Enantioselective Total Synthesis
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