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Total synthesis of (±)-helminthosporal via fragmentation reaction

✍ Scribed by Hiroto Nagaoka; Atsuo Baba; Yasuji Yamada


Book ID
104225936
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
252 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis


A new route for the total synthesis of (f)-helminthosporal ((-+)-I), involving fragmentation reaction of tricyclo[3.2.1.02~7]octane derivative 5 to give bicyclo[3.2.l]octane derivative

6 as a crucial step, is described.


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First synthesis of the naturally occurring compound (+)-ligudentatol is presented. It demonstrates the synthetic utility of the "Photoaddition-Fragmentation-Aromatic Annulation" sequence, recently developed v/a the intramolecular photocycloaddition of dihydropyrones to I alkenes.