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Unprecedented Ring Contractions in Cytochalasans: Formation of [10]cytochalasans and a cyclohepta[4,5]benz[1,2‐ d ]isoindole derivative
Author(s) -
Boutellier Markus,
Zürcher Werner,
Tamm Christoph
Publication year - 1995
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.19950780203
Subject(s) - chemistry , isoindole , derivative (finance) , pyridine , ring (chemistry) , medicinal chemistry , stereochemistry , organic chemistry , financial economics , economics
A series of transformations of cytochalasin D ( 1 ; zygosporin A) was carried out. After treatment of the diol 7 with mesyl chloride and pyridine, and subsequent chromatography on silica gel, the 17‐acetyl derivatives 12 and 13 , the first members of the hitherto unknown [10]cytochalasans, were obtained. The alcohol 8 was converted to the chlorosulfinate 18 under the same conditions. Replacement of pyridine by triethylamine in the mesylation reaction led to the cyclohepta[4,5]benz[1,2‐ d ]isoindole derivative 20 , also representing a novel ring system.