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ChemInform Abstract: Decarboxylative Photocyclization: Synthesis of Benzopyrrolizidines and Macrocyclic Lactones.

✍ Scribed by Axel G. Griesbeck; Frank Nerowski; Johann Lex

Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Decarboxylative Photocyclization: Synthesis of Benzopyrrolizidines and Macrocyclic Lactones.

-Irradiation of potassium salts of the amino acid derivatives (I), (VII), and (IX) leads to the cyclization products (II), (VIII), and (X). Product (VIII) cyclizes with high cis diastereoselectivity, whereas starting from (I) and (IX) low diastereoselectivity is observed. Remarkably, products resulting from simple decarboxylation or dimerization are not formed. Stereoselective preparation of the cis-ether (IV) by treatment of (II) with MeOH/HCOOH indicates that the trans-isomer undergoes acid-catalyzed epimerization to the cis-isomer. -(GRIESBECK, AXEL G.; NEROWSKI,

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