ChemInform Abstract: Vinyl Radical Cyclization in the Synthesis of Natural Products: Seychellene.

1986 ◽  
Vol 17 (16) ◽  
Author(s):  
G. STORK ◽  
N. H. BAINE
Keyword(s):  
Natural Products ◽  
Radical Cyclization ◽  
Vinyl Radical

Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A

2017 ◽  
Vol 4 (11) ◽  
pp. 2211-2215 ◽  
Author(s):  
Hao Zhang ◽  
Shiqiang Ma ◽  
Zhimin Xing ◽  
Lin Liu ◽  
Bowen Fang ◽  
...  
Keyword(s):  
Natural Products ◽  
Radical Cyclization ◽  
Cyclization Reaction ◽  
Rapid Construction

A tandem radical cyclization towards the 6/6/5 tricyclic skeleton, which exists in numerous natural products, was developed in modest to good yields.

scholarly journals A Vinyl Radical Cyclization Route to Hydroxycyclohexene Fused Carbocycles

2016 ◽  
Vol 28 (1) ◽  
pp. 233-234 ◽  
Author(s):  
Shiladitya Chaudhuri ◽  
Susama Maity ◽  
Mahua Roy ◽  
Paramita Ray ◽  
Jayanta K. Ray
Keyword(s):  
Radical Cyclization ◽  
Vinyl Radical

scholarly journals Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction

2013 ◽  
Vol 9 ◽  
pp. 1326-1332 ◽  
Author(s):  
Koichiro Miyazaki ◽  
Yu Yamane ◽  
Ryuichiro Yo ◽  
Hidemitsu Uno ◽  
Akio Kamimura
Keyword(s):  
Silicon Atom ◽  
Cascade Reaction ◽  
Radical Cyclization ◽  
Optically Active ◽  
Unsaturated Ester ◽  
Terminal Alkyne ◽  
Silyl Radical ◽  
Vinyl Radical ◽  
Radical Cascade ◽  
Carbonyl Radical

Bicyclodihydrosiloles were readily prepared from optically active enyne compounds by a radical cascade reaction triggered by tris(trimethylsilyl)silane ((Me3Si)3SiH). The reaction was initiated by the addition of a silyl radical to an α,β-unsaturated ester, forming an α-carbonyl radical that underwent radical cyclization to a terminal alkyne unit. The resulting vinyl radical attacked the silicon atom in an SHi manner to give dihydrosilole. The reaction preferentially formed trans isomers of bicyclosiloles with an approximately 7:3 to 9:1 selectivity.

Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines

1999 ◽  
Vol 40 (8) ◽  
pp. 1515-1518 ◽  
Author(s):  
Ilhyong Ryu ◽  
Shin-ichi Ogura ◽  
Satoshi Minakata ◽  
Mitsuo Komatsu
Keyword(s):  
Radical Cyclization ◽  
Imino Group ◽  
Vinyl Radical

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).

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