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Model Studies towards Functionalized Bisbenzannulated [5,6]‐Spiroketals
Author(s) -
Wilsdorf Michael,
Lentz Dieter,
Reissig HansUlrich
Publication year - 2016
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.201501586
Subject(s) - chemistry , regioselectivity , moiety , ketone , nucleophilic substitution , nucleophile , stereochemistry , substitution (logic) , methyl ketone , functional group , combinatorial chemistry , organic chemistry , catalysis , computer science , programming language , polymer
Following up on our previous model studies on the synthesis of simple bisbenzannulated [5,6]‐spiroketals we here report the preparation of new examples of this entity with a variation in their substitution pattern. The regioselective introduction of functional groups in the C‐3 or C‐3′ positions (rubromycin numbering) may either take place prior to the spiroketalization by α‐functionalizations of the ketone moiety of the precursor or in a subsequent step by the nucleophilic substitution of the benzylic hydroxy group of the previously described C‐3‐hydroxylated spiroketal. By applying these methods we could synthesize new methyl‐substituted, hydroxylated, halogenated and amino‐substituted bisbenzannulated [5,6]‐spiroketals in good overall yields.