Total Synthesis of (−)‐Nakadomarin A |
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| Authors: | Prof. Dr. J. Stephen Clark Dr. Chao Xu |
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| Affiliation: | 1. http://www.chem.gla.ac.uk/staff/stephenc/ 0000-0003-3935-0377 WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, UK;2. WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, UK |
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| 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. |
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| Keywords: | alkaloids natural products Overman rearrangement ring-closing metathesis total synthesis |
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