Concise Total Synthesis of Dehaloperophoramidine. Issue 5 (16th December 2015)

• Record Type: Journal Article
• Authors: Popov, Kirill; Hoang, Anita; Somfai, Peter
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 5(2016)
• Page Start: 1801
• Page End: 1804
• Publication Date: 2015-12-16
• Subjects: alkaloids -- domino reactions -- heterocycles -- natural products -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201510661
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Perophoramidine, dehaloperophoramidine, and communesin F are structurally related alkaloids having intriguing polycyclic structures. A strategy for the synthesis of dehaloperophoramidine has been developed. In this synthesis all skeletal atoms and all functional groups required to reach the target molecule are incorporated early in the sequence. This approach led to the discovery of two novel substrate‐specific domino processes, one encompassing four steps and the other comprising five steps, thus resulting in an eight‐step synthesis of dehaloperophoramidine. Abstract : Fast and furious : The eight‐step synthesis of dehaloperophoramidine, a polycyclic indole alkaloid, is achieved by incorporating two substrate‐specific domino processes. The discovery of these processes resulted from a retrosynthetic analysis in which all skeletal atoms and all functional groups required to reach the target molecule were incorporated at an early stage of the sequence.