The Synthesis of (±)‐α‐Vetispirene Via the Dieckmann Condensation of Ethyl 4‐(2,6‐Dimethyl‐1‐Carbethoxycyclohex‐2‐Enyl)‐Butyrate | Zendy

Zee ShengHsu | Zendy; Chou ShanYen | Zendy

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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 ).

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