The Total Synthesis of cis‐7,8‐Dihydroxy‐11,12‐dehydrocalamenene by Regio‐ and Diastereo‐selective Alkylation of Chiral η6‐Arenetricarbonylchromium Complexes: An Unexpected Case of Nucleophilic Aromatic tele‐Substitution with Methoxide as a Leaving Group

With complete diastereoselectivity and no loss of absolute stereochemical information, the chiral synthetic building block 1 is converted into 2, an advanced intermediate in the total synthesis of the antiinfective sesquiterpene 3. The reactivity of arene-Cr(CO)3 complexes is crucial to the synthetic strategy. TMS = SiMe3.