Synthesis of azimic acid using hydroformylation

Roderick W. Bates; Sivarajan Kasinathan

doi:10.1016/j.tet.2013.01.060

Synthesis of azimic acid using hydroformylation

Roderick W. Bates^*, Sivarajan Kasinathan

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

A synthesis of the alkaloid azimic acid has been achieved using double hydroformylation with a single tandem condensation to form the six membered ring. The oxygen substituent was introduced by diastereoselective dihydroxylation, cis to the existing alkyl substituent. The methyl substituent was introduced via an iminium ion intermediate under stereoelectronic control.

Original language	English
Pages (from-to)	3088-3092
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2013.01.060
Publication status	Published - Apr 8 2013
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Alkaloid
Hydroformylation
Iminium ion
Piperidine
Stereoselectivity

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10.1016/j.tet.2013.01.060

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abstract = "A synthesis of the alkaloid azimic acid has been achieved using double hydroformylation with a single tandem condensation to form the six membered ring. The oxygen substituent was introduced by diastereoselective dihydroxylation, cis to the existing alkyl substituent. The methyl substituent was introduced via an iminium ion intermediate under stereoelectronic control.",

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AU - Kasinathan, Sivarajan

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AB - A synthesis of the alkaloid azimic acid has been achieved using double hydroformylation with a single tandem condensation to form the six membered ring. The oxygen substituent was introduced by diastereoselective dihydroxylation, cis to the existing alkyl substituent. The methyl substituent was introduced via an iminium ion intermediate under stereoelectronic control.

KW - Alkaloid

KW - Hydroformylation

KW - Iminium ion

KW - Piperidine

KW - Stereoselectivity

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JF - Tetrahedron

IS - 14

ER -

Synthesis of azimic acid using hydroformylation

Abstract

ASJC Scopus Subject Areas

Keywords

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