Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

Hojong Yoon; Kyung Seon Cho; Taebo Sim

doi:10.1016/j.tetasy.2014.02.009

Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

Hojong Yoon, Kyung Seon Cho, Taebo Sim

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

17 Citations (Scopus)

Abstract

The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-α-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine.

Original language	English
Pages (from-to)	497-502
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	25
Issue number	6-7
DOIs	https://doi.org/10.1016/j.tetasy.2014.02.009
Publication status	Published - 2014 Apr 15

Bibliographical note

Funding Information:
This research was supported by Korea Institute of Science and Technology and a Grant ( NRF-2011-0028676 ) from the creative/challenging research program of National Research Foundation of Korea and a Grant ( D33400 ) from Korea Basic Science Institute and a Grant ( A111345 ) from the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea .

Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/j.tetasy.2014.02.009

Cite this

@article{604809c2437b48ef99d0d41f259e15da,

title = "Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach",

abstract = "The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-α-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine.",

author = "Hojong Yoon and Cho, {Kyung Seon} and Taebo Sim",

note = "Funding Information: This research was supported by Korea Institute of Science and Technology and a Grant ( NRF-2011-0028676 ) from the creative/challenging research program of National Research Foundation of Korea and a Grant ( D33400 ) from Korea Basic Science Institute and a Grant ( A111345 ) from the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea . Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",

year = "2014",

month = apr,

day = "15",

doi = "10.1016/j.tetasy.2014.02.009",

language = "English",

volume = "25",

pages = "497--502",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd",

number = "6-7",

}

TY - JOUR

T1 - Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

AU - Yoon, Hojong

AU - Cho, Kyung Seon

AU - Sim, Taebo

N1 - Funding Information: This research was supported by Korea Institute of Science and Technology and a Grant ( NRF-2011-0028676 ) from the creative/challenging research program of National Research Foundation of Korea and a Grant ( D33400 ) from Korea Basic Science Institute and a Grant ( A111345 ) from the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea . Copyright: Copyright 2014 Elsevier B.V., All rights reserved.

PY - 2014/4/15

Y1 - 2014/4/15

N2 - The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-α-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine.

AB - The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-α-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine.

UR - http://www.scopus.com/inward/record.url?scp=84898852140&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2014.02.009

DO - 10.1016/j.tetasy.2014.02.009

M3 - Article

AN - SCOPUS:84898852140

SN - 0957-4166

VL - 25

SP - 497

EP - 502

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 6-7

ER -

Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this