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Synthese von Tetradecano‐14‐lacton durch Ringerweiterung
Author(s) -
Kostova Kalina,
Hesse Manfred
Publication year - 1995
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.19950780214
Subject(s) - chemistry , stereochemistry , medicinal chemistry
Synthesis of Tetradecano‐14‐lactone by Ring Enlargement The aldehyde 3 , prepared by ozonolysis of 2‐allyl‐2‐nitrocyclododecanone, gave the ring‐enlargement product 5 (85%) by treatment with (i‐Bu) 2 AlH. Its transformation to the tetradecano‐14‐lactone ( 8 ) via the aldol ester 6 and other routes (best is reduction with Bu 3 SnH, AlBN, toluene) was difficult. Remarkable is the smooth denitrification of 3 (loss of HNO 2 ) to the conjugated dione 4 by chromatography on silica gel or base treatment.