Premium
Formal Synthesis of (±)‐Isodihydronepetalactone
Author(s) -
Chang MengYang,
Chang BoRm,
Chang ChungHo,
Chen ShuiTein,
Chang NeinChen
Publication year - 2002
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200200036
Subject(s) - chemistry , cyclopentanone , lactone , cyclobutanone , derivative (finance) , hydrazone , stereochemistry , formal synthesis , organic chemistry , catalysis , ring (chemistry) , financial economics , economics
A formal synthesis of (±)‐isodihydronepetalactone ( 1 ) from cyclobutenone 5 was de scribed. Baeyer‐Villiger lactonization of cyclobutanone 8 followed by decholorination led to lactone 4 , which under went a series of functional group trans formations, furnished cyclopentanone derivative 15 . Shapiro reaction on hydrazone derivative in the presence of excess dry ice gave lactone 2 . Lactone 2 had previously been converted to isodihydronepetalactone ( 1 ).