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Total Synthesis and Electrophysiological Properties of Natural (−)‐Perhydrohistrionicotoxin, its Unnatural (+)‐Antipode and their 2‐Depentyl Analogs
Author(s) -
Takahashi Kimio,
Witkop Bernhard,
Brossi Arnold,
Maleque Mohammed A.,
Albuquerque Edson X.
Publication year - 1982
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.19820650125
Subject(s) - chemistry , diastereomer , optically active , stereochemistry , hydrolysis , total synthesis , natural compound , enantioselective synthesis , organic chemistry , catalysis , biochemical engineering , engineering
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 LiAlH 4 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.