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Proline Sulfonamide-Catalyzed, Domino Process for Asymmetric Synthesis of Amino- and Hydroxy-Substituted Bicyclo[2.2.2]octanes

https://doi.org/10.1002/ejoc.201501302

El-Mansy, Mohamed F. ; Kang, Jun Yong ; Lingampally, Rajinikanth ; Carter, Rich G. ( January 2016 , European Journal of Organic Chemistry)

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Enantioselective Synthesis of (−)‐Halenaquinone

https://doi.org/10.1002/ange.201805370

Goswami, Subir ; Harada, Kenichi ; El‐Mansy, Mohamed F. ; Lingampally, Rajinikanth ; Carter, Rich G. ( June 2018 , Angewandte Chemie)

Abstract
The efficient, 12–14 step (LLS) total synthesis of (−)‐halenaquinone has been achieved. Key steps in the synthetic sequence include: (a) proline sulfonamide‐catalyzed, Yamada–Otani reaction to establish the C6 all‐carbon quaternary stereocenter, (b) multiple, novel palladium‐mediated oxidative cyclizations to introduce the furan moiety, and (c) oxidative Bergman cyclization to form the final quinone ring.

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Enantioselective Synthesis of (−)‐Halenaquinone

https://doi.org/10.1002/anie.201805370

Goswami, Subir ; Harada, Kenichi ; El‐Mansy, Mohamed F. ; Lingampally, Rajinikanth ; Carter, Rich G. ( June 2018 , Angewandte Chemie International Edition)

Abstract
The efficient, 12–14 step (LLS) total synthesis of (−)‐halenaquinone has been achieved. Key steps in the synthetic sequence include: (a) proline sulfonamide‐catalyzed, Yamada–Otani reaction to establish the C6 all‐carbon quaternary stereocenter, (b) multiple, novel palladium‐mediated oxidative cyclizations to introduce the furan moiety, and (c) oxidative Bergman cyclization to form the final quinone ring.

more » « less