The Aplidium haouarianum metabolite haouamine A is known for its highly strained 3-aza-[7]-paracyclophane core. We developed a promising approach toward this marine tunicate-derived alkaloid, which includes an efficient Suzuki cross-coupling reaction, an aldol condensation, and an aromatization process. No less than seven late-stage intermediates were analyzed by X-ray diffraction to provide valuable and reliable information about the relationships between conformation and reactivity.

Synthetic studies toward haouamine A

240th National Meeting (2010)

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