Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine

Robert J. Moreau; Erik J. Sorensen

doi:10.1016/j.tet.2007.03.024

Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine

Robert J. Moreau
, Erik J. Sorensen

Chemistry

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

30 Scopus citations

Abstract

The development of a direct synthesis of the complex core topology of the alkaloid acutumine from a simple keto proline derivative is described. An efficient sequence of three carbonyl-dependent reactions is at the heart of this design for synthesis.

Original language	English (US)
Pages (from-to)	6446-6453
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	28
DOIs	https://doi.org/10.1016/j.tet.2007.03.024
State	Published - Jul 9 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Acutumine
Chlorine-containing alkaloids
Dieckmann condensation
Michael reaction
The carbonyl group
β-Elimination

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10.1016/j.tet.2007.03.024

Cite this

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title = "Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine",

abstract = "The development of a direct synthesis of the complex core topology of the alkaloid acutumine from a simple keto proline derivative is described. An efficient sequence of three carbonyl-dependent reactions is at the heart of this design for synthesis.",

keywords = "Acutumine, Chlorine-containing alkaloids, Dieckmann condensation, Michael reaction, The carbonyl group, β-Elimination",

author = "Moreau, \{Robert J.\} and Sorensen, \{Erik J.\}",

note = "Funding Information: This work was supported by the National Institute of General Medical Sciences (GM074763), Merck Research Laboratories, Boehringer Ingelheim, a Johnson \& Johnson Focused Giving Award (E.J.S.), Princeton University, and a predoctoral fellowship from Bristol-Myers Squibb (R.J.M.). We thank Dr. G{\"u}nther Scheid for his early efforts on this project, particularly on the quinone-based route. We also thank Dr. Istv{\'a}n Pelczer and Dr. Carlos Pacheco (Princeton) for NMR assistance, and Dr. Gary Siuzdak (The Scripps Research Institute) for mass spectral analysis. ",

year = "2007",

month = jul,

day = "9",

doi = "10.1016/j.tet.2007.03.024",

language = "English (US)",

volume = "63",

pages = "6446--6453",

journal = "Tetrahedron",

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TY - JOUR

T1 - Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine

AU - Moreau, Robert J.

AU - Sorensen, Erik J.

N1 - Funding Information: This work was supported by the National Institute of General Medical Sciences (GM074763), Merck Research Laboratories, Boehringer Ingelheim, a Johnson & Johnson Focused Giving Award (E.J.S.), Princeton University, and a predoctoral fellowship from Bristol-Myers Squibb (R.J.M.). We thank Dr. Günther Scheid for his early efforts on this project, particularly on the quinone-based route. We also thank Dr. István Pelczer and Dr. Carlos Pacheco (Princeton) for NMR assistance, and Dr. Gary Siuzdak (The Scripps Research Institute) for mass spectral analysis.

PY - 2007/7/9

Y1 - 2007/7/9

N2 - The development of a direct synthesis of the complex core topology of the alkaloid acutumine from a simple keto proline derivative is described. An efficient sequence of three carbonyl-dependent reactions is at the heart of this design for synthesis.

AB - The development of a direct synthesis of the complex core topology of the alkaloid acutumine from a simple keto proline derivative is described. An efficient sequence of three carbonyl-dependent reactions is at the heart of this design for synthesis.

KW - Acutumine

KW - Chlorine-containing alkaloids

KW - Dieckmann condensation

KW - Michael reaction

KW - The carbonyl group

KW - β-Elimination

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UR - https://www.scopus.com/pages/publications/34249342315#tab=citedBy

U2 - 10.1016/j.tet.2007.03.024

DO - 10.1016/j.tet.2007.03.024

M3 - Article

AN - SCOPUS:34249342315

SN - 0040-4020

VL - 63

SP - 6446

EP - 6453

JO - Tetrahedron

JF - Tetrahedron

IS - 28

ER -

Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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