Total Synthesis of the Norhasubanan Alkaloid Stephadiamine

Nina Hartrampf, Nils Winter, Gabriele Pupo, Brian M. Stoltz, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

(+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent α-tertiary amines, which renders it an attractive synthetic target. Here, we present the first total synthesis of stephadiamine, which hinges on an efficient cascade reaction to implement the aza[4.3.3]propellane core of the alkaloid. The α-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. Useful building blocks for the asymmetric synthesis of morphine and (nor)hasubanan alkaloids are introduced.

Original languageEnglish (US)
Pages (from-to)8675-8680
Number of pages6
JournalJournal of the American Chemical Society
Volume140
Issue number28
DOIs
StatePublished - Jul 18 2018

Fingerprint

Alkaloids
Stephania
Hinges
Skeleton
Morphine
Amines

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Hartrampf, N., Winter, N., Pupo, G., Stoltz, B. M., & Trauner, D. (2018). Total Synthesis of the Norhasubanan Alkaloid Stephadiamine. Journal of the American Chemical Society, 140(28), 8675-8680. https://doi.org/10.1021/jacs.8b01918

Total Synthesis of the Norhasubanan Alkaloid Stephadiamine. / Hartrampf, Nina; Winter, Nils; Pupo, Gabriele; Stoltz, Brian M.; Trauner, Dirk.

In: Journal of the American Chemical Society, Vol. 140, No. 28, 18.07.2018, p. 8675-8680.

Research output: Contribution to journalArticle

Hartrampf, N, Winter, N, Pupo, G, Stoltz, BM & Trauner, D 2018, 'Total Synthesis of the Norhasubanan Alkaloid Stephadiamine', Journal of the American Chemical Society, vol. 140, no. 28, pp. 8675-8680. https://doi.org/10.1021/jacs.8b01918
Hartrampf, Nina ; Winter, Nils ; Pupo, Gabriele ; Stoltz, Brian M. ; Trauner, Dirk. / Total Synthesis of the Norhasubanan Alkaloid Stephadiamine. In: Journal of the American Chemical Society. 2018 ; Vol. 140, No. 28. pp. 8675-8680.
@article{20e5833b991b475a9b971337bfb53350,
title = "Total Synthesis of the Norhasubanan Alkaloid Stephadiamine",
abstract = "(+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent α-tertiary amines, which renders it an attractive synthetic target. Here, we present the first total synthesis of stephadiamine, which hinges on an efficient cascade reaction to implement the aza[4.3.3]propellane core of the alkaloid. The α-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. Useful building blocks for the asymmetric synthesis of morphine and (nor)hasubanan alkaloids are introduced.",
author = "Nina Hartrampf and Nils Winter and Gabriele Pupo and Stoltz, {Brian M.} and Dirk Trauner",
year = "2018",
month = "7",
day = "18",
doi = "10.1021/jacs.8b01918",
language = "English (US)",
volume = "140",
pages = "8675--8680",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "28",

}

TY - JOUR

T1 - Total Synthesis of the Norhasubanan Alkaloid Stephadiamine

AU - Hartrampf, Nina

AU - Winter, Nils

AU - Pupo, Gabriele

AU - Stoltz, Brian M.

AU - Trauner, Dirk

PY - 2018/7/18

Y1 - 2018/7/18

N2 - (+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent α-tertiary amines, which renders it an attractive synthetic target. Here, we present the first total synthesis of stephadiamine, which hinges on an efficient cascade reaction to implement the aza[4.3.3]propellane core of the alkaloid. The α-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. Useful building blocks for the asymmetric synthesis of morphine and (nor)hasubanan alkaloids are introduced.

AB - (+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent α-tertiary amines, which renders it an attractive synthetic target. Here, we present the first total synthesis of stephadiamine, which hinges on an efficient cascade reaction to implement the aza[4.3.3]propellane core of the alkaloid. The α-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. Useful building blocks for the asymmetric synthesis of morphine and (nor)hasubanan alkaloids are introduced.

UR - http://www.scopus.com/inward/record.url?scp=85048714488&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85048714488&partnerID=8YFLogxK

U2 - 10.1021/jacs.8b01918

DO - 10.1021/jacs.8b01918

M3 - Article

VL - 140

SP - 8675

EP - 8680

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 28

ER -