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- Title
Total Synthesis of (−)-Nakadomarin A.
- Authors
Clark, J. Stephen; Xu, Chao
- 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.
- Subjects
KETONE derivatives; ASYMMETRIC synthesis; ALKALOID synthesis; METATHESIS reactions; RING formation (Chemistry); REARRANGEMENTS (Chemistry); AMINATION
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 13, p4404
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201600990