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.

Metal-Free Cascade Methylation/Cyclization of N-Alkyl-N-methacryloylbenzamides with Dicumyl Peroxide

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 617-620 ◽  
Author(s):  
Yan-Ning Niu ◽  
Xiao-Feng Xia ◽  
Yuan Yuan
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Metal Free ◽  
Wide Range ◽  
Radical Cascade ◽  
Convenient Access

A metal-free radical cascade methylation/cyclization of a wide range of N-alkyl-N-methacryloylbenzamides by using dicumyl peroxide as the methylating reagent provides a convenient access to a series of methylated isoquinoline-1,3-diones in moderate yields.

Metal-free radical cascade dichloromethylation of activated alkenes using CH2Cl2: highly selective activation of the C–H bond

RSC Advances ◽  
2014 ◽  
Vol 4 (110) ◽  
pp. 64855-64859 ◽  
Author(s):  
Yunfei Tian ◽  
Zhong-Quan Liu
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Cascade Process ◽  
Selective Activation ◽  
Metal Free ◽  
Efficient Access ◽  
Radical Cascade

A dicumyl peroxide-initiated highly selective activation of the (sp3)C–H bond in dichloromethane (DCM, CH2Cl2) has been achieved, which allows efficient access to dichloronated oxindoles via a free-radical cascade process.

ChemInform Abstract: TOTAL SYNTHESIS OF SATIVENE AND COPACAMPHENE VIA A FREE RADICAL CYCLIZATION

1977 ◽  
Vol 8 (2) ◽  
pp. no-no
Author(s):  
P. BAKUZIS ◽  
O. O. S. CAMPOS ◽  
M. L. F. BAKUZIS
Keyword(s):  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization

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).

New Entry to γ-Butyrolactams by Free Radical Cyclization ofN-Allyl-α-chloro-α-(methylthio)acetamides. Formal Total Synthesis of (±)-Pseudoheliotridane

1987 ◽  
Vol 16 (5) ◽  
pp. 795-798 ◽  
Author(s):  
Hiroyuki Ishibashi ◽  
Tatsunori Sato ◽  
Maki Irie ◽  
Suzumi Harada ◽  
Masazumi Ikeda
Keyword(s):  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
New Entry

Biomimetic total synthesis of (±)-yezo'otogirin A

2014 ◽  
Vol 12 (16) ◽  
pp. 2519-2522 ◽  
Author(s):  
Hiu C. Lam ◽  
Kevin K. W. Kuan ◽  
Jonathan H. George
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Radical Cyclization ◽  
Biosynthetic Precursor ◽  
Oxidative Radical Cyclization

A concise total synthesis of (±)-yezo'otogirin A has been achieved via its presumed biosynthetic precursor using a late-stage biomimetic oxidative radical cyclization.

Total synthesis of (R)-Argentilactone and (R)-Goniothalamin using a Free Radical Photoredox Approach to α,β-Unsaturated δ-Lactones.

Synthesis ◽  
2021 ◽  
Author(s):  
Francisco Javier Fuentes-Pantoja ◽  
Alejandro Cordero-Vargas
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Free Radical ◽  
Total Synthesis ◽  
Research Group ◽  
Structural Motifs ◽  
New Approach ◽  
Unsaturated Lactone ◽  
Pharmacologically Active ◽  
Active Natural

α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)-goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-unsaturated δ-lactones.

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