Total Synthesis and Electrophysiological Properties of Natural (−)-Perhydrohistrionicotoxin,its Unnatural (+)-Antipode and their 2-Depentyl Analogs |
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Authors: | Kimio Takahashi Bernhard Witkop Arnold Brossi Mohammed A. Maleque Edson X. Albuquerque |
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Abstract: | Natural (?)-perhydrohistrionicotoxin ( 6a ), its unnatural (+)-antipode 6b , (?)-2-depentylperhydrohistrionicotoxin ( 7a ) and its (+)-antipode 7b have been prepared and characterized. Kishi's lactam 8 reacted with optically active iso-cyanates, and the mixture of diastereomeric carbamates so obtained was separated and hydrolyzed yielding the optical antipodes of Kishi's lactam in optically pure form. Reduction with LiAlH4 yielded the optically active 2-depentyl analogs, while another sequence already developed in the racemic series afforded the natural toxin and its (+)-antipode. Some electrophysiological properties of these compounds are presented. |
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