Efficient Oxa-Diels–Alder/Semipinacol Rearrangement/Aldol Cascade Reaction: Short Approach to Polycyclic Architectures

• DOI: 10.1021/acs.orglett.5b00125
• Publication Date: 2015-02-09T18:51:15Z
• Authors: Jin-Bao Peng; Yue Qi; Ze-Ran Jing; Shao-Hua Wang; Yong-Qiang Tu; Dao-Yong Zhu; Fu-Min Zhang
• Keywords: Stereocenter; Aldol reaction

A novel carbon electrophile induced intermolecular oxa-Diels-Alder/semipinacol rearrangement/aldol cascade reaction of allylic silyl ether with β,γ-unsaturated α-ketoester has been developed under the promotion SnCl4. This highly efficient transformation enables quick construction polycyclic architectures up to five contiguous stereogenic centers in a single operation moderate good yields as well high diastereoselectivity and would provide versatile short approaches frameworks and/or analogues numerous biologically important natural products.