Showing papers by "Glenn M. Sammis published in 2009"
TL;DR: An efficient method for the rapid construction of carbo- and heterocycles has been developed using radical relay cyclizations initiated by alkoxy radicals, utilized as a key step in the synthesis of the tetrahydrofuran fragment in (-)-amphidinolide K.
57 citations
TL;DR: Nitrogen-centered radical cyclizations onto silyl enol ethers were utilized for the syntheses of protected polyhydroxylated pyrrolidines 2-Hydroxymethyl-3-hydroxypyrrolidine and 1-4-dideoxy-1,4-imino-L-ribitol.
17 citations
TL;DR: A new oxygen-centered radical cyclization onto silyl enol ethers has been developed and utilized for the synthesis of versatile siloxy-substituted tetrahydrofurans.
Abstract: A new oxygen-centered radical cyclization onto silyl enol ethers has been developed and utilized for the synthesis of versatile siloxy-substituted tetrahydrofurans. The reactions display excellent chemoselectivity for cyclization onto the electron-rich silyl enol ether when competing terminal alkene cyclization, 1,5-hydrogen abstraction, and beta-fragmentation pathways are present. The increased chemoselectivity also allows for the synthesis of tetrahydropyrans, a challenging substrate class to access using oxygen-centered radical alkene cyclizations due to competing 1,5-hydrogen abstractions.
2 citations
TL;DR: In this article, an efficient method for the rapid construction of carbo-and heterocycles has been developed using radical relay cyclizations initiated by alkoxy radicals, which was used as a key step in the synthesis of the tetrahydrofuran fragment in (−)-amphidinolide K.
Abstract: An efficient method for the rapid construction of carbo- and heterocycles has been developed using radical relay cyclizations initiated by alkoxy radicals. Linear substrates were cyclized to form a wide range of cyclopentane, pyrrolidine, tetrahydropyran, and tetrahydrofuran derivatives in excellent yields. This methodology was utilized as a key step in the synthesis of the tetrahydrofuran fragment in (−)-amphidinolide K.
1 citations