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Updated: Sep 24, 2025
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
RCM approach to the CDE-tricyclic structure of nakiterpiosin
Yoe Matsuyuki1, Keisuke Fukaya1, Daisuke Urabe1
1Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, Japan.
Abstract:
A synthetic approach to the CDE-tricyclic structure of nakiterpiosin, a marine-derived antimitotic C-nor-D-homosteroid, is reported. The trans-disubstituted indanone was synthesized from a commercially available carboxylic acid in 9 steps, and the ring closing metathesis of the indanone constructed the trans-fused 5/6-membered ring system. The present approach enables the concise synthesis of the functionalized CDE-tricyclic structure, which will serve as a synthetic intermediate toward nakiterpiosin.
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