Biomimetic total synthesis of the pentacyclic Amaryllidaceae alkaloid derivative gracilamine

Nadia Gao; Martin G. Banwell; Anthony C. Willis

doi:10.1021/acs.orglett.6b03465

Biomimetic total synthesis of the pentacyclic Amaryllidaceae alkaloid derivative gracilamine

Nadia Gao, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

The illustrated azomethine ylide, produced through a Schiff base condensation of the corresponding aldehydecontaining C3a-arylhexahydroindole with ethyl L-leucinate, engages in a stereoselective intramolecular cycloaddition reaction to give adduct 23 that has been elaborated, over eight steps, into the racemic modification of the alkaloid derivative gracilamine (1). The formation of this ylide and its conversion into isomer 23 mimics the proposed biogenesis of the pentacyclic framework of compound 1.

Original language	English
Pages (from-to)	162-165
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.6b03465
Publication status	Published - 6 Jan 2017

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abstract = "The illustrated azomethine ylide, produced through a Schiff base condensation of the corresponding aldehydecontaining C3a-arylhexahydroindole with ethyl L-leucinate, engages in a stereoselective intramolecular cycloaddition reaction to give adduct 23 that has been elaborated, over eight steps, into the racemic modification of the alkaloid derivative gracilamine (1). The formation of this ylide and its conversion into isomer 23 mimics the proposed biogenesis of the pentacyclic framework of compound 1.",

author = "Nadia Gao and Banwell, {Martin G.} and Willis, {Anthony C.}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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AU - Willis, Anthony C.

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N2 - The illustrated azomethine ylide, produced through a Schiff base condensation of the corresponding aldehydecontaining C3a-arylhexahydroindole with ethyl L-leucinate, engages in a stereoselective intramolecular cycloaddition reaction to give adduct 23 that has been elaborated, over eight steps, into the racemic modification of the alkaloid derivative gracilamine (1). The formation of this ylide and its conversion into isomer 23 mimics the proposed biogenesis of the pentacyclic framework of compound 1.

AB - The illustrated azomethine ylide, produced through a Schiff base condensation of the corresponding aldehydecontaining C3a-arylhexahydroindole with ethyl L-leucinate, engages in a stereoselective intramolecular cycloaddition reaction to give adduct 23 that has been elaborated, over eight steps, into the racemic modification of the alkaloid derivative gracilamine (1). The formation of this ylide and its conversion into isomer 23 mimics the proposed biogenesis of the pentacyclic framework of compound 1.

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DO - 10.1021/acs.orglett.6b03465

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JO - Organic Letters

JF - Organic Letters

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Biomimetic total synthesis of the pentacyclic Amaryllidaceae alkaloid derivative gracilamine

Abstract

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