ChemInform Abstract: Total Syntheses of (.+-.)-Anchinopeptolide D and (.+-.)-Cycloanchinopeptolide D.
Abstract
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ChemInform Abstract
The synthesis of anchinopeptolide D (IV) is achieved via stereoselective dimerization of the keto amide (II). On irradiation in water (IV) undergoes [2 + 2] cycloaddition to afford cycloanchinopeptolide D (V). The cyclobutane ring is formed by an unprecedented head-to-head dimerization of the hydroxystyrylamide units. Additionally, it is found that naturally occurring glutamyl-N-[2-(4-hydroxyphenyl)ethenyl]glycinamide adopts the structure (VI) and not an acyclic structure as previously reported.
