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A new olefination protocol utilizing ethyl bromoacetate was highlighted, in which magnesium enolate of the ester coupled with C 20 dialdehyde 6 , and double eliminations of the protected hydroxyl groups and bromine atoms of the coupling bromohydrin product, efficiently produced norbixin 1 after concomitant hydrolysis of the ester. A new (C 7 + C 10 + C 7 ) disconnection approach was demonstrated for the synthesis of norbixin ethyl ester 2 by the Julia-Kocienski olefination of novel C 7 benzothiazolyl-sulfone 11 and C 10 2,7-dimethyl-2,4,6-octatrienedial ( 12 ).

Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses