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Synthesis of the FGHI Ring System of Azaspiracid
Author(s) -
Nicolaou K. C.,
Pihko Petri M.,
Diedrichs Nicole,
Zou Ning,
Bernal Federico
Publication year - 2001
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 - 10.1002/1521-3773(20010401)40:7<1262::aid-anie1262>3.0.co;2-9
Subject(s) - ring (chemistry) , marine toxin , intramolecular force , chemistry , mytilus , stereochemistry , diastereomer , combinatorial chemistry , organic chemistry , fishery , biology , toxin , biochemistry
As a causative agent of food poisonings, azaspiracid ( 1 ), a novel marine toxin isolated from the mussel Mytilus edulis , challenges the synthetic chemist with an intricate array of acetal and ketal structures. The construction of the FGHI ring system of azaspiracid was achieved by means of a key BF 3 ⋅Et 2 O‐catalyzed cyclization to form the HI spirocycle. A final chemoselective intramolecular ketalization with Hg(OAc) 2 formed the G ring, to afford the N‐protected FGHI as a single diastereomer.