Described herein is a concise synthetic strategy of tetracyclic homoisoflavanoids from commercially available substituted acetophenones. Several reported strategies involve more than 8 steps with low overall yields. In this work, a one-pot Heck coupling/2H-chromenization followed by a chemoselective reduction cleared the path for a cis-diastereoselective dihydroxylation. Efficient access to these biologically relevant natural products will facilitate the synthesis of analogs and derivatives designed from structure-activity-relationship studies and shed light to improved construction of a chromane skeleton cis-fused with an indane moiety.

Total synthesis of tetracyclic homoisoflavanoids from the heartwood of <i>Caesalpinia sappan</i>

ACS Spring 2022

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Total synthesis of tetracyclic homoisoflavanoids from the heartwood of Caesalpinia sappan