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Synthesis of Pheromones with Acetal Structures via Radical CC Bond Formation
Author(s) -
Giese Bernd,
Bartmann Dieter,
Haßkerl Thomas
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870348
Subject(s) - chemistry , ketone , acetal , propene , methyl vinyl ketone , alkyl , medicinal chemistry , double bond , organic chemistry , stereochemistry , catalysis
Spirocyclic acetals 4a, 4b and exo ‐brevicomin ( 5 ) are synthesized as racemates via radical additions to divinyl ketone and methyl vinyl ketone, respectively. Radical precursors are the alkyl mercuric salt 6 and iodides 9a,9b , which can easily be generated via solvomercuration of propene and 1‐penten‐3‐ol ( 8 ), respectively. Reduction of the ketone groups under the reducing conditions of these radical chain reactions was not observed.