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Stereocontrolled Synthesis of (−)‐5,11‐Dideoxytetrodotoxin
Author(s) -
Nishikawa Toshio,
Asai Masanori,
Ohyabu Norio,
Yamamoto Noboru,
Isobe Minoru
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19991018)38:20<3081::aid-anie3081>3.0.co;2-6
Subject(s) - chemistry
New derivatives of an intriguing marine natural product are now accessible. The first asymmetric synthesis of the simple tetrodotoxin analogue, 5,11‐dideoxytetrodotoxin ( 3 ), was achieved. Hydroxylation at position C8 of the key intermediate 1 relied on the neighboring trichloroacetamide group, and stereoselective elaboration of the vinyl group gave α ‐hydroxylactone 2 , which was transformed into the title compound through a new guanidylation method.