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Solvolytic hydroperoxide rearrangements V. A stereoselective synthesis of trans-fused butyrolactones.

✍ Scribed by Suzanne M. Ruder; Robert C. Ronald

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 240 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95668-5

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✦ Synopsis

Stereoselective rearrangement of cis-5-(4-methaxybenzyl)-spiro[5,2]-octan-4-01

cis-1 in acidified THF-90% H202 affords 9-oxabicyclo[6.2.l]nonyl hydroperoxides 7 and 8 which are converted to medium-ring, keto-butyrolactones 2 and 3.

In the previous paper we have described a stereoselective rearrangement of spiro[5,2]octan-4-01 in high strength H202 which resulted in ring-expansion with overall inversion of configuration at the carbinyl centerl.

We report herein how this rearrangement may be exploited in a short and efficient synthesis of keto-lactones 2 and 3. Our strategy

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