Getting to the center of it: The strategy for an efficient asymmetric synthesis of the D-ring subunit embedded in massadine (1) includes: application of a cationic norbornyl rearrangement, ozonolytic cleavage displaying remarkable end-group differentiation, and a carboxy-inversion reaction for the installation of the hindered secondary alcohol.
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Breder et al. (2008) studied this question.
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