title: Total Synthesis of (-)-Nakadomarin A.
abstract: A highly efficient 12-step synthesis of the marine alkaloid (-)-nakadomarin A has been accomplished. The key advanced intermediate, a tetracyclic ketone derivative, was constructed in just seven steps using a sequence that includes an asymmetric Pauson-Khand reaction, an Overman rearrangement reaction, a ring-closing metathesis reaction, and an amination reaction. Late introduction of the furan ring during the synthesis of (-)-nakadomarin A means that the key tetracyclic ketone derivative has the potential to serve as an advanced intermediate for the synthesis of related marine alkaloids.
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK. stephen.clark@glasgow.ac.uk.
authors.forename: J Stephen
authors.identifier: http://orcid.org/0000-0003-3935-0377
authors.initials: JS
authors.lastname: Clark
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK.
authors.forename: Chao
authors.initials: C
authors.lastname: Xu
mesh_terms: D002243:Carbolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; C476640:nakadomarin A
keywords: Overman rearrangement; alkaloids; natural products; ring-closing metathesis; total synthesis