Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction

Ashkaan Younai, Gregory F. Chin, Jared T. Shaw

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The first synthesis of heliotropamide is reported. The preparation of this 2-oxopyrrolidine (γ-lactam) natural product relied on a diastereoselective one-pot, four-component reaction (4CR) for the assembly of the core structure. On the basis of chemical shift correlation and NOESY experiments, the previously unknown alkene geometry of heliotropamide is assigned as E.

Original languageEnglish (US)
Pages (from-to)8333-8336
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number23
DOIs
StatePublished - Dec 3 2010

Fingerprint

Lactams
Chemical shift
Alkenes
Biological Products
Geometry
Experiments
heliotropamide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction. / Younai, Ashkaan; Chin, Gregory F.; Shaw, Jared T.

In: Journal of Organic Chemistry, Vol. 75, No. 23, 03.12.2010, p. 8333-8336.

Research output: Contribution to journalArticle

Younai, Ashkaan ; Chin, Gregory F. ; Shaw, Jared T. / Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction. In: Journal of Organic Chemistry. 2010 ; Vol. 75, No. 23. pp. 8333-8336.
@article{151818d332664538ae48616e76a3fbdf,
title = "Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction",
abstract = "The first synthesis of heliotropamide is reported. The preparation of this 2-oxopyrrolidine (γ-lactam) natural product relied on a diastereoselective one-pot, four-component reaction (4CR) for the assembly of the core structure. On the basis of chemical shift correlation and NOESY experiments, the previously unknown alkene geometry of heliotropamide is assigned as E.",
author = "Ashkaan Younai and Chin, {Gregory F.} and Shaw, {Jared T.}",
year = "2010",
month = "12",
day = "3",
doi = "10.1021/jo1019317",
language = "English (US)",
volume = "75",
pages = "8333--8336",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "23",

}

TY - JOUR

T1 - Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction

AU - Younai, Ashkaan

AU - Chin, Gregory F.

AU - Shaw, Jared T.

PY - 2010/12/3

Y1 - 2010/12/3

N2 - The first synthesis of heliotropamide is reported. The preparation of this 2-oxopyrrolidine (γ-lactam) natural product relied on a diastereoselective one-pot, four-component reaction (4CR) for the assembly of the core structure. On the basis of chemical shift correlation and NOESY experiments, the previously unknown alkene geometry of heliotropamide is assigned as E.

AB - The first synthesis of heliotropamide is reported. The preparation of this 2-oxopyrrolidine (γ-lactam) natural product relied on a diastereoselective one-pot, four-component reaction (4CR) for the assembly of the core structure. On the basis of chemical shift correlation and NOESY experiments, the previously unknown alkene geometry of heliotropamide is assigned as E.

UR - http://www.scopus.com/inward/record.url?scp=78650260965&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78650260965&partnerID=8YFLogxK

U2 - 10.1021/jo1019317

DO - 10.1021/jo1019317

M3 - Article

C2 - 21062051

AN - SCOPUS:78650260965

VL - 75

SP - 8333

EP - 8336

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -