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Total Synthesis of (−)‐Nakadomarin A
Author(s) -
Clark J. Stephen,
Xu Chao
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201600990
Subject(s) - salt metathesis reaction , ketone , derivative (finance) , metathesis , total synthesis , chemistry , ring closing metathesis , furan , amination , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , polymerization , polymer , financial economics , economics
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.