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Total Synthesis of (−)-Nakadomarin A

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2013-10-18

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Cheng, Bichu. 2013. Total Synthesis of (−)-Nakadomarin A. Doctoral dissertation, Harvard University.

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Abstract

A convergent and scalable total synthesis of polycyclic manzamine alkaloid (-)-nakadomarin A is described. Unsaturated bicyclic lactam fragment A was prepared from acrolein in 5 steps, and macrolactam fragment B was prepared from 3-furfural in 7 steps. A double Michael addition reaction (or cyclization) between A and B provided the desired fragment coupling product C in 79% yield and 9:1 dr on more than one-gram scale. Completion of the total synthesis of (-)-nakadomarin A was then achieved in a one-pot transformation from compound C.

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Chemistry

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