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Updated: May 21, 2026
![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
One-pot approach to installing eight-membered rings onto indoles
Can Zhu1, Xue Zhang, Xiongdong Lian
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
Abstract:
Ring fusion: The Pd(0)-catalyzed reaction of 2-allyl-3-iodo-1-tosyl-1H-indoles and propargylic bromides affords dihydrocycloocta[b]indoles (see scheme; M.S. = molecular sieves, TFP = tris(2-furyl)phosphine, Ts = 4-toluenemethanesulfonyl), and proceeds by carbon-carbon coupling, [1,5]-hydrogen migration, and electrocyclization. The newly established method was used to efficiently access iprindole.
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