Achiral auxiliary-assisted chiral transfer via microwave-accelerated aza-Claisen rearrangement: A short synthesis of (+)-1-hydroxyquinolizidinone

Jaehoon Sim; Hwayoung Yun; Jong Wha Jung; Sujin Lee; Nam Jung Kim; Young Ger Suh

doi:10.1016/j.tetlet.2012.06.073

Achiral auxiliary-assisted chiral transfer via microwave-accelerated aza-Claisen rearrangement: A short synthesis of (+)-1-hydroxyquinolizidinone

Jaehoon Sim, Hwayoung Yun, Jong Wha Jung, Sujin Lee, Nam Jung Kim, Young Ger Suh

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

12 Citations (Scopus)

Abstract

A short and efficient synthesis of (+)-1-hydroxyquinolizidinone as an advanced core intermediate for the syntheses of (+)-epiquinamide, (+)-homopumiliotoxin, and (+)-lupinine is described. The key feature of our strategy includes a sequential chiral transfer using an achiral phenylsulfide auxiliary via microwave-accelerated aza-Claisen rearrangement of the unexplored N-thiophenoxyacetyl-α-vinyl piperidine substrate and the oxone-induced transannulation.

Original language	English
Pages (from-to)	4813-4815
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2012.06.073
Publication status	Published - 5 Sept 2012

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea Grant funded by the Korean Government (MEST) (NRF-C1ABA001-2010-0020428)

Keywords

(+)-1-Hydroxyquinolizidinone
Achiral auxiliary
Quinolizidine alkaloid
Transannulation
aza-Claisen rearrangement

Access to Document

10.1016/j.tetlet.2012.06.073

Cite this

@article{6210bda4d55e41e483fa1066ac4653db,

title = "Achiral auxiliary-assisted chiral transfer via microwave-accelerated aza-Claisen rearrangement: A short synthesis of (+)-1-hydroxyquinolizidinone",

abstract = "A short and efficient synthesis of (+)-1-hydroxyquinolizidinone as an advanced core intermediate for the syntheses of (+)-epiquinamide, (+)-homopumiliotoxin, and (+)-lupinine is described. The key feature of our strategy includes a sequential chiral transfer using an achiral phenylsulfide auxiliary via microwave-accelerated aza-Claisen rearrangement of the unexplored N-thiophenoxyacetyl-α-vinyl piperidine substrate and the oxone-induced transannulation.",

keywords = "(+)-1-Hydroxyquinolizidinone, Achiral auxiliary, Quinolizidine alkaloid, Transannulation, aza-Claisen rearrangement",

author = "Jaehoon Sim and Hwayoung Yun and Jung, {Jong Wha} and Sujin Lee and Kim, {Nam Jung} and Suh, {Young Ger}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea Grant funded by the Korean Government (MEST) (NRF-C1ABA001-2010-0020428)",

year = "2012",

month = sep,

day = "5",

doi = "10.1016/j.tetlet.2012.06.073",

language = "English",

volume = "53",

pages = "4813--4815",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "36",

}

TY - JOUR

T1 - Achiral auxiliary-assisted chiral transfer via microwave-accelerated aza-Claisen rearrangement

T2 - A short synthesis of (+)-1-hydroxyquinolizidinone

AU - Sim, Jaehoon

AU - Yun, Hwayoung

AU - Jung, Jong Wha

AU - Lee, Sujin

AU - Kim, Nam Jung

AU - Suh, Young Ger

N1 - Funding Information: This work was supported by the National Research Foundation of Korea Grant funded by the Korean Government (MEST) (NRF-C1ABA001-2010-0020428)

PY - 2012/9/5

Y1 - 2012/9/5

N2 - A short and efficient synthesis of (+)-1-hydroxyquinolizidinone as an advanced core intermediate for the syntheses of (+)-epiquinamide, (+)-homopumiliotoxin, and (+)-lupinine is described. The key feature of our strategy includes a sequential chiral transfer using an achiral phenylsulfide auxiliary via microwave-accelerated aza-Claisen rearrangement of the unexplored N-thiophenoxyacetyl-α-vinyl piperidine substrate and the oxone-induced transannulation.

AB - A short and efficient synthesis of (+)-1-hydroxyquinolizidinone as an advanced core intermediate for the syntheses of (+)-epiquinamide, (+)-homopumiliotoxin, and (+)-lupinine is described. The key feature of our strategy includes a sequential chiral transfer using an achiral phenylsulfide auxiliary via microwave-accelerated aza-Claisen rearrangement of the unexplored N-thiophenoxyacetyl-α-vinyl piperidine substrate and the oxone-induced transannulation.

KW - (+)-1-Hydroxyquinolizidinone

KW - Achiral auxiliary

KW - Quinolizidine alkaloid

KW - Transannulation

KW - aza-Claisen rearrangement

UR - http://www.scopus.com/inward/record.url?scp=84864442980&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.06.073

DO - 10.1016/j.tetlet.2012.06.073

M3 - Article

AN - SCOPUS:84864442980

SN - 0040-4039

VL - 53

SP - 4813

EP - 4815

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Achiral auxiliary-assisted chiral transfer via microwave-accelerated aza-Claisen rearrangement: A short synthesis of (+)-1-hydroxyquinolizidinone

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this