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. 2019 Jun 7;4(6):10019-10024.
doi: 10.1021/acsomega.9b00900. eCollection 2019 Jun 30.

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

Dahye Kim  1 , Mohammad Shariful Alam  1 , Wook-Jin Chung  1 , Sangho Koo  1
Affiliations

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

Dahye Kim et al. ACS Omega. .

Abstract

A new olefination protocol utilizing ethyl bromoacetate was highlighted, in which magnesium enolate of the ester coupled with C20 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 (C7 + C10 + C7) disconnection approach was demonstrated for the synthesis of norbixin ethyl ester 2 by the Julia-Kocienski olefination of novel C7 benzothiazolyl-sulfone 11 and C10 2,7-dimethyl-2,4,6-octatrienedial (12).

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Norbixin 1 and its ethyl ester 2 and their synthetic strategies.
Figure 2
Figure 2
Intermediate structures in norbixin synthesis from ethyl bromoacetate (5c) and C20 dial 6.
Scheme 1
Scheme 1. Synthesis of Norbixin Ethyl Ester 2 by Julia–Kocienski Olefination
See this image and copyright information in PMC

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