Chirality transmission involving a free-radical-mediated 6-exo cyclization process. Stereocontrolled synthesis of branched-chain 1,4-diols

1990 ◽  
Vol 112 (22) ◽  
pp. 8175-8177 ◽  
Author(s):  
Masato Koreeda ◽  
Lawrence G. Hamann
Keyword(s):  
Free Radical ◽  
Cyclization Process ◽  
Stereocontrolled Synthesis ◽  
Branched Chain

Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3′-C-trifluoromethyl and 3′-C-methyl pyranonucleosides

2015 ◽  
Vol 407 ◽  
pp. 170-178 ◽  
Author(s):  
Nikolaos Kollatos ◽  
Stella Manta ◽  
Athina Dimopoulou ◽  
Vanessa Parmenopoulou ◽  
Virginia V. Triantakonstanti ◽  
...  
Keyword(s):  
Stereocontrolled Synthesis ◽  
Branched Chain

Synthesis of C-4 branched-chain furanoses by free radical-mediated cyclization

1989 ◽  
Vol 194 ◽  
pp. C1-C3 ◽  
Author(s):  
Kwan Soo Kim ◽  
Jung Hee Kim ◽  
Young Kwan Kim ◽  
Yong Sun Park ◽  
Chi Sun Hahn
Keyword(s):  
Free Radical ◽  
Branched Chain

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.

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