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    Synthesis of 12,12′-azo-13,13′-diepi-Ritterazine N (2017)
    American Chemical Society
    In:  The Journal of Organic Chemistry, 82 (1). pp. 269-275.
    Details
    Publication Date: 2020-01-02
    Description: A synthesis of the 12,12′-azo-analogue of ritterazine N from hecogenin is reported. Ring contraction of two 6/5 bicyclic ring systems, one trans-fused and another spiro, to 5/5 spiro ring systems is accomplished with excellent stereochemical control. Key transformations include an abnormal Baeyer–Villiger oxidation, a Norrish type I cleavage, an intramolecular dipolar [3 + 2] cycloaddition, and an intramolecular oxymecuration. Failing to uncover the β-OH ketone from the isoxazoline ring, we end up with a synthesis of a cyclic analogue of ritterazine N.
    Type: Article , PeerReviewed
    Format: text
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