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Design and Synthesis of Spirocyclics Via the Diels Alder Reaction and Ring-Opening Cross-Metathesis as Key Steps

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Ring-opening-cross-metathesis (ROCM) reaction has been used to prepare spiro-indane derivatives containing six rings. The Diels-Alder (DA) chemistry of indan-2-spiro(cyclopenta-2,4-diene) 1 with various dienophiles such as 1,4-benzoquinone and its derivatives gave the corresponding DA products in moderate to good yields. Also, we report an improved procedure for preparation of the spiro-diene 1 using phase-transfer catalysis (PTC) conditions.

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Keywords: Diels-Alder; Fenestranes; Grubbs' Catalyst; Quinones; ROCM; Spiro-diene; Spirocycles

Document Type: Research Article

Affiliations: Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai-400076, India.

Publication date: 2006-02-01

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