A chemoenzymatic total synthesis of the Amaryllidaceae alkaloid narseronine

Brett D. Schwartz; Martin G. Banwell; Ian A. Cade

doi:10.1016/j.tetlet.2011.06.050

A chemoenzymatic total synthesis of the Amaryllidaceae alkaloid narseronine

Brett D. Schwartz, Martin G. Banwell^*, Ian A. Cade

^*Corresponding author for this work

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

27 Citations (Scopus)

Abstract

A 15-step and fully stereocontrolled total synthesis of the title alkaloid 1 has been accomplished using the enantiomerically pure and enzymatically- derived cis-1,2-dihydrocatechol 2 as starting material. The final and pivotal step involved the intramolecular hetero-Michael addition of secondary amine 16 to a tethered enone moiety followed by trapping of the resulting enolate through its reaction with an adjacent ester residue.

Original language	English
Pages (from-to)	4526-4528
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2011.06.050
Publication status	Published - 31 Aug 2011

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10.1016/j.tetlet.2011.06.050

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title = "A chemoenzymatic total synthesis of the Amaryllidaceae alkaloid narseronine",

abstract = "A 15-step and fully stereocontrolled total synthesis of the title alkaloid 1 has been accomplished using the enantiomerically pure and enzymatically- derived cis-1,2-dihydrocatechol 2 as starting material. The final and pivotal step involved the intramolecular hetero-Michael addition of secondary amine 16 to a tethered enone moiety followed by trapping of the resulting enolate through its reaction with an adjacent ester residue.",

keywords = "Alkaloid, Chemoenzymatic, Michael addition, Narseronine, Natural product synthesis",

author = "Schwartz, {Brett D.} and Banwell, {Martin G.} and Cade, {Ian A.}",

year = "2011",

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AU - Banwell, Martin G.

AU - Cade, Ian A.

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Y1 - 2011/8/31

N2 - A 15-step and fully stereocontrolled total synthesis of the title alkaloid 1 has been accomplished using the enantiomerically pure and enzymatically- derived cis-1,2-dihydrocatechol 2 as starting material. The final and pivotal step involved the intramolecular hetero-Michael addition of secondary amine 16 to a tethered enone moiety followed by trapping of the resulting enolate through its reaction with an adjacent ester residue.

AB - A 15-step and fully stereocontrolled total synthesis of the title alkaloid 1 has been accomplished using the enantiomerically pure and enzymatically- derived cis-1,2-dihydrocatechol 2 as starting material. The final and pivotal step involved the intramolecular hetero-Michael addition of secondary amine 16 to a tethered enone moiety followed by trapping of the resulting enolate through its reaction with an adjacent ester residue.

KW - Alkaloid

KW - Chemoenzymatic

KW - Michael addition

KW - Narseronine

KW - Natural product synthesis

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U2 - 10.1016/j.tetlet.2011.06.050

DO - 10.1016/j.tetlet.2011.06.050

M3 - Article

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SP - 4526

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

A chemoenzymatic total synthesis of the Amaryllidaceae alkaloid narseronine

Abstract

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