Abstract

AbstractAn approach to the total synthesis of crassifoside F, a natural product isolated from Curculigo crassifolia with ACE (angiotensin‐converting enzyme) inhibitory activity, has been developed. An intramolecular SN2 reaction has been employed as the key reaction to construct the central oxygen rich core. The glucosyl‐fused eight‐membered cyclic skeleton present in this natural product is unique and has been formed via a AuI catalyzed novel glycosidation reaction using a 1,2‐propargyl orthoester and different asymmetric reactions. Moreover, this ring has been selected as a handle to control the stereochemistry.

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