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Synthesis of a Constitutional Isomer of Nerol by Consecutive Ireland–Claisen and Cope Rearrangements
Author(s) -
Kraft Philip,
Eichenberger Walter,
Fráter Georg
Publication year - 1999
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/(sici)1099-0690(199911)1999:11<2781::aid-ejoc2781>3.0.co;2-c
Subject(s) - chemistry , nerol , claisen rearrangement , cope rearrangement , stereochemistry , organic chemistry , geraniol , chromatography , essential oil
(2 Z ,6 E )‐3,6‐Dimethylocta‐2,6‐dien‐1‐ol ( 6 ) was synthesized by Steglich esterification of (2 E )‐2‐methylbut‐2‐en‐1‐ol (tiglic alcohol, 7 ) with 3‐methylbut‐2‐en‐1‐oic acid (senecioic acid, 8 ), followed by selective Ireland–Claisen rearrangement of the resulting ester 9 at 0°C and subsequent Cope rearrangement of the product at 140°C. A standard LAH reduction in the last step of the synthetic sequence transformed the α,β‐unsaturated acid 12 into the target molecule 6 , a constitutional isomer of nerol ( 5 ) with interesting olfactory properties.