Total Synthesis of (−)-Nakadomarin A

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 reacti...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-03, Vol.55 (13), p.4332-4335
Main Authors: Clark, J. Stephen, Xu, Chao
Format: Article
Language:English
Subjects:
Alkaloids
Amination
Carbolines - chemical synthesis
Chemical synthesis
Ketones
Metathesis
natural products
Overman rearrangement
ring-closing metathesis
Stereoisomerism
total synthesis
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Summary: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. The later the better: A highly efficient 12‐step synthesis of (−)‐nakadomarin A is reported. The key tetracyclic ketone intermediate was constructed from a simple enyne in seven steps. As the furan is introduced at a later synthetic stage, this intermediate may have potential in the syntheses of related marine alkaloids such as manzamine A and ircinal A.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201600990