alexa Biomimetic total synthesis of litseaverticillols B, E, I, and J and structural reassignment of litseaverticillol E.
Genetics & Molecular Biology

Genetics & Molecular Biology

Journal of Molecular and Genetic Medicine

Author(s): Vassilikogiannakis G, Margaros I, Montagnon T

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Abstract [reaction: see text] The first total synthesis of litseaverticillols B (1), E (2), I (4), and J (5) as well as the structural reassignment of litseaverticillol E (2) have been achieved by means of a biomimetic sequence of transformations during which a [4 + 2]-initiated reaction cascade and an ene reaction, both involving singlet oxygen ((1)O(2)), formed key steps. The reassignment of the structure of litseaverticillol E (3) to include an allylic hydroperoxide provides strong support for our biogenetic hypothesis. This article was published in Org Lett and referenced in Journal of Molecular and Genetic Medicine

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