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Total Synthesis of (−)‐Nakadomarin A
Author(s) -
Clark J. Stephen,
Xu Chao
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600990
Subject(s) - ketone , salt metathesis reaction , derivative (finance) , chemistry , metathesis , total synthesis , ring closing metathesis , furan , amination , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , financial economics , economics , polymerization , polymer
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.