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Ring expansion route to cycloheptane derivatives

✍ Scribed by Stephen A. Monti; Thomas W. McAninch

Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
126 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

The development of new methods for the construction of odd-membered rings, particularly five-and seven-membered cycles, has been stimulated by the increasing number of biologically active, naturally occurring substances which contain these structural characteristics.2 We wish to report an efficient, general method for the preparation of functionalized seven-membered rings via a one-carbon ring expansion3 of cyclohexane derivatives. This transformation involves the cleavage of the internal bond of a bicyclo[4.l.O]heptane moiety by a thermal homoCl,5]hydrogen shift or enolene rearrangement'+ as shown'in eq 1.

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## Abstract magnified image Lactonization of 2‐(hydroxymethyl)‐5‐isopropenyl‐4,5‐dihydrofuran‐3‐carboxylic acids **1a,b,c** with dicyclohexylcarbodiimide gave the corresponding furano‐lactones, 5‐isopropenyl‐5,6‐dihydro‐1(3__H__)‐furo[3,4‐__b__]furanone **2a,b,c**, which were readily converted to