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

Dahye Kim | Zendy; Mohammad Shariful Alam | Zendy; Wook–Jin Chung | Zendy; Sangho Koo | Zendy

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

Author(s) -

Dahye Kim,

Mohammad Shariful Alam,

Wook–Jin Chung,

Sangho Koo

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b00900

Subject(s) - ethyl bromoacetate , sulfone , chemistry , hydrolysis , organic chemistry , magnesium

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 ).

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