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Pectenotoxin's ABCDE Ring System: A Complex Target to Test the Potential of Singlet Oxygen Super Cascades as Tools for Synthesis
Author(s) -
Kouridaki Antonia,
Sofiadis Manolis,
Montag Tamsyn,
Vassilikogiannakis Georgios
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501095
Subject(s) - cascade , chemistry , singlet oxygen , octane , ring (chemistry) , substrate (aquarium) , sequence (biology) , cascade reaction , combinatorial chemistry , stereochemistry , singlet state , oxygen , organic chemistry , atomic physics , physics , biochemistry , oceanography , chromatography , excited state , geology , catalysis
A difuran substrate was synthesized that then participated in a singlet oxygen mediated super cascade reaction sequence to give the ABCDE ring skeleton of certain pectenotoxins. During this super cascade, two separate reaction sequences occurred in parallel to create both the [6,6]‐spiroketal and the 2,8‐dioxabicyclo[3.2.1]octane motifs in one synthetic operation.