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A Novel Three‐Carbon Ring Expansion Sequence Synthesis of Exaltone ® and (±)‐Muscone
Author(s) -
Fehr Charles
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660816
Subject(s) - chemistry , intramolecular force , carbanion , ring (chemistry) , nucleophile , sequence (biology) , stereochemistry , grignard reaction , sulfone , carbon fibers , medicinal chemistry , organic chemistry , catalysis , biochemistry , materials science , reagent , composite number , composite material
Intramolecular Grignard ‐type reaction of the bromo lactones 3 and 8 affords the macrocycles 10, 11, 12 and 13, 14, 15 , respectively. More efficiently, 10 and 13 are obtained by intramolecular nucleophilic attack of the carbanions derived from the sulfonyl lactones 20 and 22 and in situ reduction of the intermediate sulfones 21 and 23. The macrocylic hydroxy ketones 10 and 13 are converted into Exaltone ® (2) and muscone (1) , respectively.