 Three key disconnections arising from an element of perceived symmetry in the indoxamycin F skeleton serve as a testing ground for several modern C-H functionalization methodologies in a complex moleuclar setting. A failed C-H insertion/Cope reaction process led to the serendipitous discovery of a rhodium(II)-carbenoid C-H insertion into a pseudo-symmetrical [3.3.0]-bicyclooctane, establishing the first key bond targeted for disconnection with absolute regio- and diastereoselectivity.

Progress toward indoxamycin F utilizing modern C-H functionalization methods

247th National Meeting (2014)

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