Premium
The Synthesis of (±)‐α‐Vetispirene Via the Dieckmann Condensation of Ethyl 4‐(2,6‐Dimethyl‐1‐Carbethoxycyclohex‐2‐Enyl)‐Butyrate
Author(s) -
Zee ShengHsu,
Chou ShanYen
Publication year - 1988
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.198800044
Subject(s) - chemistry , yield (engineering) , alkylation , condensation , stereoselectivity , butyrate , organic chemistry , ethyl butyrate , ethyl acetate , catalysis , physics , fermentation , thermodynamics , materials science , metallurgy
A new process for the synthesis of (±)‐α‐vetispirene ( 1 ) starting from 2,4‐dimethyl‐3‐carbethaxycyclohexene ( 2 ) is described. The key steps include the stereoselective alkylation of 2 with ethyl 4‐bromo‐butyrate to yield ethyl 4‐(2,6‐dimethyl‐1‐carbethoxycyctohex‐2‐enyl)‐bytyrate ( 3 ) and spiroannulation of 3 by Dieckmann condensation to give 2‐carbethoxy‐6,10‐dimethyl spiro[4,5] deca‐6‐en‐1‐one ( 4 ).