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A new convergent synthesis of (±)‐methyl jasmonate based on a C4 + C6 synthon approach
Author(s) -
Jaunky Piotr,
Buirey Julien,
Mahaim Cyril
Publication year - 2017
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3391
Subject(s) - synthon , methyl jasmonate , chemistry , yield (engineering) , chloride , magnesium , stereochemistry , acetyl chloride , organic chemistry , catalysis , biochemistry , materials science , metallurgy , gene
A new, convergent synthesis of (±)‐methyl jasmonate is presented. The strategy is based on a C4+C6 synthon approach. The C4 fragment N,4,4‐trimethoxy‐N‐methyl‐butanamide ( 5 ) was prepared in 4 steps starting from chloroacetyl chloride via the previously unreported N,4,4‐trimethoxy‐N‐methylbut‐2‐enamide ( 4 ). The coupling of 5 with the C6 synthon, cis ‐3‐hexenyl magnesium chloride ( 6 ), provided easy access to ( Z )‐4‐oxodec‐7‐enal ( 8 ). The latter was converted to the key intermediate ( Z )‐2‐(pent‐2‐en‐1‐yl)cyclopent‐2‐en‐1‐one ( 9 ) from which (±)‐methyl jasmonate can be obtained in high yield using well‐established procedures.