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Approaches to the total synthesis of cytochalasans. A convergent synthesis of the octahydroisoindolone moiety related to proxiphomin. Preliminary communication
Author(s) -
Schmidlin Tibur,
Tamm Christoph
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610616
Subject(s) - chemistry , moiety , malonate , derivative (finance) , convergent synthesis , intramolecular force , ring (chemistry) , cycloaddition , stereochemistry , yield (engineering) , total synthesis , lactam , ethylene , medicinal chemistry , organic chemistry , materials science , financial economics , economics , metallurgy , catalysis
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.