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Synthesis of (+-)-grandisol

✍ Scribed by Billups, W. E.; Cross, J. H.; Smith, C. V.

Book ID
121197654
Publisher
American Chemical Society
Year
1973
Tongue
English
Weight
279 KB
Volume
95
Category
Article
ISSN
0002-7863

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A New Stereoselective Synthesis of Grand
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## Abstract Grandisol (10) is stereoselectively synthesized in 9 steps, starting from commercially available 3‐methyl‐3‐buten‐1‐ol (1). The key step of the synthesis is the Cu(I)‐catalyzed [2 + 2]‐photocycloaddition of 3 to 4a or 4b. Moreover, solvent effects on the __endo/exo__ product ratio of th

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## Abstract The natural and (+)‐enantiomer of grandisol [1, (1__R__,2__S__)‐(+)‐2‐isopropenyl‐1‐methylcyclobutaneethanol] has been synthesized from (__R__)‐(—)‐carvone (2) by employing the intramolecular alkylation of 8 to give 9 as the key step.