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General methods of alkaloid synthesis. XIII. the total synthesis of (±)-ipalbidine and (±)-septicine

✍ Scribed by Robert V. Stevens; Yuhshi Luh

Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 178 KB
Volume: 18
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)92807-2

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✦ Synopsis

Recently, we reported' the total synthesis of (*)-isoretronecanol (1) and (+)-8-coniceine (2).

A key step in each of these syntheses utilized the acid-catalyzed rearrangement of a cyclopropylimine to generate the 3-phenylthio-2-pyrroline synthon (2). The latter intermediate serves as a relatively stable equivalent synthon for the corresponding unstable unsubstituted endocyclic enamine 4. We now report the application of this methodology to the synthesis of the more complex indolizidine alkaloids (+)-ipalbidine (5b)2 and (+)-septicine (!).

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