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Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin. / Coote, Susannah C.; Moore, Stephen P.; O'Brien, Peter et al.
In: Journal of Organic Chemistry, Vol. 73, No. 19, 03.10.2008, p. 7852-7855.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Coote, SC, Moore, SP, O'Brien, P, Whitwood, AC & Gilday, J 2008, 'Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin', Journal of Organic Chemistry, vol. 73, no. 19, pp. 7852-7855. https://doi.org/10.1021/jo801586h

APA

Coote, S. C., Moore, S. P., O'Brien, P., Whitwood, A. C., & Gilday, J. (2008). Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin. Journal of Organic Chemistry, 73(19), 7852-7855. https://doi.org/10.1021/jo801586h

Vancouver

Coote SC, Moore SP, O'Brien P, Whitwood AC, Gilday J. Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin. Journal of Organic Chemistry. 2008 Oct 3;73(19):7852-7855. doi: 10.1021/jo801586h

Author

Coote, Susannah C. ; Moore, Stephen P. ; O'Brien, Peter et al. / Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides : effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin. In: Journal of Organic Chemistry. 2008 ; Vol. 73, No. 19. pp. 7852-7855.

Bibtex

@article{1bd7b37332654d4191fd3b6e69ef0078,
title = "Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin",
abstract = "In 18 out of 20 examples of the organolithium-mediated conversion of beta-alkoxy aziridines into substituted allylic sulfonamides, use of a Bus (Bus = t-BuSO(2)) substituent on the nitrogen gave higher yields compared to the analogous N-Ts compounds. The success with the N-Bus aziridines facilitated the development of a new route to the spirocyclic core of the histrionicotoxins and completion of a formal synthesis of (+/-)-perhydrohistrionicotoxin.",
keywords = "TERMINAL AZIRIDINES, LITHIATION, AMINES, ALCOHOLS, OXIRANYL, REAGENTS, OLEFINS, UTILITY, ANIONS, ROUTE",
author = "Coote, {Susannah C.} and Moore, {Stephen P.} and Peter O'Brien and Whitwood, {Adrian C.} and John Gilday",
year = "2008",
month = oct,
day = "3",
doi = "10.1021/jo801586h",
language = "English",
volume = "73",
pages = "7852--7855",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "19",

}

RIS

TY - JOUR

T1 - Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides

T2 - effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin

AU - Coote, Susannah C.

AU - Moore, Stephen P.

AU - O'Brien, Peter

AU - Whitwood, Adrian C.

AU - Gilday, John

PY - 2008/10/3

Y1 - 2008/10/3

N2 - In 18 out of 20 examples of the organolithium-mediated conversion of beta-alkoxy aziridines into substituted allylic sulfonamides, use of a Bus (Bus = t-BuSO(2)) substituent on the nitrogen gave higher yields compared to the analogous N-Ts compounds. The success with the N-Bus aziridines facilitated the development of a new route to the spirocyclic core of the histrionicotoxins and completion of a formal synthesis of (+/-)-perhydrohistrionicotoxin.

AB - In 18 out of 20 examples of the organolithium-mediated conversion of beta-alkoxy aziridines into substituted allylic sulfonamides, use of a Bus (Bus = t-BuSO(2)) substituent on the nitrogen gave higher yields compared to the analogous N-Ts compounds. The success with the N-Bus aziridines facilitated the development of a new route to the spirocyclic core of the histrionicotoxins and completion of a formal synthesis of (+/-)-perhydrohistrionicotoxin.

KW - TERMINAL AZIRIDINES

KW - LITHIATION

KW - AMINES

KW - ALCOHOLS

KW - OXIRANYL

KW - REAGENTS

KW - OLEFINS

KW - UTILITY

KW - ANIONS

KW - ROUTE

U2 - 10.1021/jo801586h

DO - 10.1021/jo801586h

M3 - Journal article

VL - 73

SP - 7852

EP - 7855

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -