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Studies toward the AB ring system of the tetrapetalone natural products.

ABSTRACT: Synthetic efforts toward the rapid assembly of the AB ring system of the tetrapetalones is described. Key to this work was the use of [3+2] cycloaddition/oxidative extrusion methodology to furnish functionalized aryl enones. The Nazarov cyclization of these substrates was examined, and optimized to generate the AB ring carbon skeleton. Then, Pd-catalyzed cross-coupling were conducted, and conditions were identified that enabled installation of the requisite C14-N bond.

SUBMITTER: Carlsen P 

PROVIDER: S-EPMC4542023 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Studies toward the AB ring system of the tetrapetalone natural products.

Carlsen Peter P   Jiang Chao C   Herrick Ildiko R IR   Frontier Alison J AJ  

Tetrahedron 20150901 35

Synthetic efforts toward the rapid assembly of the AB ring system of the tetrapetalones is described. Key to this work was the use of [3+2] cycloaddition/oxidative extrusion methodology to furnish functionalized aryl enones. The Nazarov cyclization of these substrates was examined, and optimized to generate the AB ring carbon skeleton. Then, Pd-catalyzed cross-coupling were conducted, and conditions were identified that enabled installation of the requisite C14-N bond. ...[more]

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