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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.

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: February 1, 2006

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.

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