Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
J Org Chem. 2010 Nov 5;75(21):7052-60. doi: 10.1021/jo101598y.
A total synthesis of (-)-callipeltoside A (1) has been achieved. The core macrocycle was made via a dual macrolactonization/pyran hemiketal formation reaction, developed to circumvent issues related to the reversible nature of acylketene formation from β-keto lactone substrates. Initial approaches to the core of the natural product that revolved around ring-closing metathesis (RCM) and relay ring-closing metathesis (RRCM) reactions are also described.
(-)-callipeltoside A(1)的全合成已经完成。该核心大环通过双内酯化/吡喃半缩醛形成反应构建,该反应的开发是为了避免与β-酮内酯底物形成酰基炔的可逆性相关的问题。还描述了最初围绕闭环复分解(RCM)和接力闭环复分解(RRCM)反应的天然产物核心的方法。