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

Sambasivarao      Kotha; Ashoke   C.   Deb; Subrata      Chattopadhyay

Letters in Organic Chemistry

Author(s): Sambasivarao Kotha, Ashoke C. Deb and Subrata Chattopadhyay

DOI: 10.2174/157017806775224350

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

Page: [128 - 134] Pages: 7

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Abstract

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

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