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2. Synthesis of Fused Oxepane HIV Integrase Inhibitor MK-1376.

Author

Maligres, Peter E., Song, Zhiguo Jake, Strotman, Neil A., Yin, Jinquin, Pei, Tao, Strotman, Hallena R., Itoh, Tetsuji, Sherer, Edward C., and Humphrey, Guy R.

Subjects
HIV integrase inhibitors, QUINONE, STEREOCHEMISTRY, ALLYLATION
Abstract

Controlling the absolute and relative stereochemistry of a seven-membered oxepane in the formation of HIV integrase inhibitor MK-1376 was accomplished through a strategy involving the use of asymmetric allylation and stereoconvergent, substrate-directed installation of an amine fragment. Surprising reactivity was demonstrated during the asymmetric allylation in which the allyl-pyrimidone product was formed reversibly. The stereoconvergent amine addition was accomplished through an elimination/addition sequence involving a quinone methide reactive intermediate, and nucleophilic trapping of the reactive quinone methide intermediate with methylamine. This novel approach delivered MK-1376, offering 100-fold greater productivity and 50-fold less waste than the initial synthetic chemistry route. [ABSTRACT FROM AUTHOR]

Published
2020
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4. A Traceless Directing Group for CH Borylation.

Author

Preshlock, Sean M., Plattner, Donald L., Maligres, Peter E., Krska, Shane W., Maleczka, Robert E., and Smith, Milton R.

Subjects
CARBON-hydrogen bonds, HETEROCYCLIC compounds, ANILINE, AROMATIC amines, GROUP 13 elements
Abstract

Not a trace: Borylation of the nitrogen in nitrogen heterocycles or anilines provides a traceless directing group for subsequent catalytic CH borylation. Selectivities that previously required Boc protection can be achieved; furthermore, the NBpin directing group can be installed and removed in situ, and product yields are substantially higher. Boc=tert‐butoxycarbonyl, pin=pinacolato. [ABSTRACT FROM AUTHOR]

Published
2013
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5. A Traceless Directing Group for CH Borylation.

Author

Preshlock, Sean M., Plattner, Donald L., Maligres, Peter E., Krska, Shane W., Maleczka, Robert E., and Smith, Milton R.

Subjects
HETEROCYCLIC compounds, BORENES, ANILINE, NITROGEN, CHEMICAL research
Abstract

Keine Spur: Die Borylierung des Stickstoffatoms in Stickstoffheterocyclen oder Anilinen liefert eine spurlose dirigierende Gruppe für die anschließende katalytische C ‐ H ‐ Borylierung. Selektivitäten, für die früher Boc ‐ Schützung notwendig war, können erzielt werden; zudem kann die NBpin ‐ Schutzgruppe in situ aufgebaut und entfernt werden, und die erzielten Ausbeuten sind deutlich höher. Boc=tert ‐ Butoxycarbonyl, pin=Pinacolato. [ABSTRACT FROM AUTHOR]

Published
2013
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