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Beyond the medium ring: A [4 + 4] cycloaddition/fragmentation synthesis of eleven-membered rings

✍ Scribed by Scott McN. Sieburth; Taleb H. Al-Tel; David Rucando


Book ID
104258317
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
118 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


Reduction of the polycyclic product of intramolecular 2-pyridone photocycloaddition with lithium/ammonia yields a functionalized cycloundecane, via an apparent multi-step reaction sequence.


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A 5, 7-membered fused-ring compound with a fianctionalized angular substituent, 8-methoxy-8act-methoxymethyl-7-phenylthio-1, 2, 3, 6-tetrahydro-3acq 613-epoxyazulene, was synthesized via a tandem Pummerer rearrangement and intramolecular [4+3] cycloaddition.