Total synthesis of (-)-raumacline

Patrick D. Bailey; Paul D. Clingan; Timothy J. Mills; Richard A. Price; Robin G. Pritchard

doi:10.1039/b310274b

Total synthesis of (-)-raumacline

Patrick D. Bailey, Paul D. Clingan, Timothy J. Mills, Richard A. Price, Robin G. Pritchard

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

Abstract

The total synthesis of (-)-raumacline from L-tryptophan was achieved, featuring a cis-specific Pictet-Spengler reaction, a stereoselective Dieckmann cyclization, and an epimerization step that allowed complete stereocontrol of five chiral centres.

Original language	English
Pages (from-to)	2800-2801
Number of pages	1
Journal	Chemical Communications
Volume	9
Issue number	22
DOIs	https://doi.org/10.1039/b310274b
Publication status	Published - 21 Nov 2003

Keywords

Cyclocondensation reaction (Pictet-Spengler, stereoselective; total synthesis of raumacline and deethyl raumacline via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization); Alkaloids Role: PNU (Preparation, unclassified), SPN (Synthetic preparation), PREP (Preparation) (indole; prepn. of the tetracyclic core of ajmaline alkaloids via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization); Crystal structure (of deethyl raumacline intermediate); Dieckmann condensation (stereoselective; total synthesis of raumacline and deethyl raumacline via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization); Asymmetric synthesis and induction (total synthesis of raumacline and deethyl raumacline via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization)

Access to Document

10.1039/b310274b

CCDC 207148: Experimental Crystal Structure Determination
Bailey, P. (Contributor), Clingan, P. D. (Contributor), Mills, T. J. (Contributor), Price, R. A. (Contributor) & Pritchard, R. (Contributor), Cambridge Crystallographic Data Centre, 28 Mar 2003
DOI: 10.5517/cc6yk6w, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6yk6w&sid=DataCite
Dataset

Cite this

@article{3adfa029c5e644cfb5c1e98f81b2565d,

title = "Total synthesis of (-)-raumacline",

abstract = "The total synthesis of (-)-raumacline from L-tryptophan was achieved, featuring a cis-specific Pictet-Spengler reaction, a stereoselective Dieckmann cyclization, and an epimerization step that allowed complete stereocontrol of five chiral centres.",

keywords = "Cyclocondensation reaction (Pictet-Spengler, stereoselective; total synthesis of raumacline and deethyl raumacline via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization); Alkaloids Role: PNU (Preparation, unclassified), SPN (Synthetic preparation), PREP (Preparation) (indole; prepn. of the tetracyclic core of ajmaline alkaloids via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization); Crystal structure (of deethyl raumacline intermediate); Dieckmann condensation (stereoselective; total synthesis of raumacline and deethyl raumacline via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization); Asymmetric synthesis and induction (total synthesis of raumacline and deethyl raumacline via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization)",

author = "Bailey, {Patrick D.} and Clingan, {Paul D.} and Mills, {Timothy J.} and Price, {Richard A.} and Pritchard, {Robin G.}",

year = "2003",

month = nov,

day = "21",

doi = "10.1039/b310274b",

language = "English",

volume = "9",

pages = "2800--2801",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "22",

}

TY - JOUR

T1 - Total synthesis of (-)-raumacline

AU - Bailey, Patrick D.

AU - Clingan, Paul D.

AU - Mills, Timothy J.

AU - Price, Richard A.

AU - Pritchard, Robin G.

PY - 2003/11/21

Y1 - 2003/11/21

N2 - The total synthesis of (-)-raumacline from L-tryptophan was achieved, featuring a cis-specific Pictet-Spengler reaction, a stereoselective Dieckmann cyclization, and an epimerization step that allowed complete stereocontrol of five chiral centres.

AB - The total synthesis of (-)-raumacline from L-tryptophan was achieved, featuring a cis-specific Pictet-Spengler reaction, a stereoselective Dieckmann cyclization, and an epimerization step that allowed complete stereocontrol of five chiral centres.

KW - Cyclocondensation reaction (Pictet-Spengler, stereoselective; total synthesis of raumacline and deethyl raumacline via cis-specific Pictet-Spengler reaction and stereoselective Dieckmann cyclization); Alkaloids Role: PNU (Preparation, unclassified), SPN (

U2 - 10.1039/b310274b

DO - 10.1039/b310274b

M3 - Article

SN - 1359-7345

VL - 9

SP - 2800

EP - 2801

JO - Chemical Communications

JF - Chemical Communications

IS - 22

ER -

Total synthesis of (-)-raumacline

Abstract

Keywords

Access to Document

Fingerprint

Datasets

CCDC 207148: Experimental Crystal Structure Determination

Cite this