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Approaches to the total synthesis of cytochalasans. A convergent synthesis of the octahydroisoindolone moiety related to proxiphomin. Preliminary communication

✍ Scribed by Tibur Schmidlin; Christoph Tamm

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
218 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The octahydroisoindolone moiety related to proxiphomin (1) has been synthesized by condensation of N‐benzyloxycarbonyl‐protected D, L‐phenylalaninal (7) with methyl‐(4‐methyl‐sorbyl)‐malonate (11) to yield the branched ethylene derivative 12. Consecutive intramolecular [2+4]‐cycloaddition and lactam ring closure of 12 gave the desired octahydroisoindolone derivative 15, possessing adaptable functional groups for the attachment of the macrocyclic ring system.

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