scholarly journals Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Carmen Pérez Morales ◽  
M. Mar Herrador ◽  
José F. Quílez del Moral ◽  
Alejandro F. Barrero
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Common Precursor ◽  
Enantiospecific Synthesis ◽  
Optically Pure

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

Synthetic approaches to [5,6]-benzannulated spiroketal natural products

2011 ◽  
Vol 84 (6) ◽  
pp. 1379-1390 ◽  
Author(s):  
Michael C. McLeod ◽  
Margaret A. Brimble ◽  
Dominea C. K. Rathwell ◽  
Zoe E. Wilson ◽  
Tsz-Ying Yuen
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Electronic Properties ◽  
Late Stage ◽  
Biologically Active ◽  
Formal Synthesis ◽  
Berkelic Acid ◽  
Synthetic Approaches

Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.

Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C

Synthesis ◽  
2020 ◽  
Author(s):  
Luis D. Miranda ◽  
Jazmín García-Ramírez
Keyword(s):  
Natural Products ◽  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Oxidative Cyclization ◽  
Dicumyl Peroxide ◽  
Cyclization Process ◽  
Radical Cascade ◽  
Oxidative Radical Cyclization

AbstractAn efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N-3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.

scholarly journals Enantioselective Total Synthesis of Otteliones A and B, Novel and Powerful Antitumor Agents from the Freshwater Plant Ottelia alismoides

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Tadashi Katoh
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Anticancer Agents ◽  
Antitumor Agents ◽  
Formal Synthesis ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Significant Attention

Otteliones A and B isolated from the freshwater plant Ottelia alismoides have attracted significant attention because of their potential as novel anticancer agents. In this review four independent enantioselective total syntheses and one formal synthesis of these natural products are presented with particular focus on their methodology and strategy.

scholarly journals Total Synthesis of Oxepin and Dihydrooxepin Containing Natural Products

Synthesis ◽  
2021 ◽  
Author(s):  
Thomas Magauer ◽  
Kevin Rafael Sokol
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Radical Cyclization ◽  
Sigmatropic Rearrangement ◽  
Natural Product Synthesis ◽  
Synthetic Methods ◽  
Acid Catalyzed ◽  
Metal Catalyzed ◽  
Key Steps

AbstractThe construction of oxepin and dihydrooxepin containing natural products represents a challenging task in total synthesis. In the last decades, a variety of synthetic methods have been reported for the installation of these structural motifs. Herein, we provide an overview of synthetic methods and strategies to construct these motifs in the context of natural product synthesis and highlight the key steps of each example.1 Introduction2 Oxepin Natural Products3 Dihydrooxepin Natural Products3 Brønsted or Lewis acid Catalyzed Cyclization3.2 Radical Cyclization3.3 Substitution and Addition Cyclization3.4 Sigmatropic Rearrangement3.5 Oxidative Methods3.6 Transition Metal Catalyzed Cyclization4 Summary

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