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A Convenient Preparation of 3-Substituted Furans: Synthesis of Perillene and Dendrolasin.

✍ Scribed by D. K. Barma; Abhijit Kundu; Rachid Baati; Charles Mioskowski; J. R. Falck

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
33
Category
Article
ISSN
0931-7597

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## Abstract Starting from 3‐bromofuran (1) or 3‐bromothiophene (2) via alkylation in 2‐position (β†’ 3–8) followed by the corresponding second alkylation in 3‐position, we obtained rose furan (9), rose thiophene (10), and their analogs 11–16. From the Ξ±,β‐unsaturated esters 17–20 by hydrogenation (β†’

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3-Substituted furan can be readily prepared in a single step via a tandem Diels-Alder/ retro Diels-Alder reaction between 4-phenyloxazole and simple alkylacetylenes. 3-Substituted furans are a somewhat difficult class of compounds to prepare. For example, the two most common methods of functionalizi