Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine

Baeck Kyoung Lee; Hwan Geun Choi; Eun Joo Roh; Won Koo Lee; Taebo Sim

doi:10.1016/j.tetlet.2012.11.087

Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine

Baeck Kyoung Lee, Hwan Geun Choi, Eun Joo Roh, Won Koo Lee, Taebo Sim

KU-KIST Graduate School of Converging Science and Technology

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

18 Citations (Scopus)

Abstract

An efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (-)-8-epi-swainsonine.

Original language	English
Pages (from-to)	553-556
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2012.11.087
Publication status	Published - 2013 Feb 6

Keywords

(-)-8-Epi-swainsonine
Aziridine
Indolizidine alkaloids
Natural product
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.11.087

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title = "Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine",

abstract = "An efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (-)-8-epi-swainsonine.",

keywords = "(-)-8-Epi-swainsonine, Aziridine, Indolizidine alkaloids, Natural product, Total synthesis",

author = "Lee, {Baeck Kyoung} and Choi, {Hwan Geun} and Roh, {Eun Joo} and Lee, {Won Koo} and Taebo Sim",

note = "Funding Information: This research was supported by the Korea Institute of Science and Technology and a Grant (No. 2011-0028676 ) from the creative/challenging research program of the National Research Foundation of Korea funded by the Ministry of Education, Science and Technology , and a Grant (No.: A111345 ) of the Korea Health technology R&D Project, Ministry of Health & Welfare, Republic of Korea. ",

year = "2013",

month = feb,

day = "6",

doi = "10.1016/j.tetlet.2012.11.087",

language = "English",

volume = "54",

pages = "553--556",

journal = "Tetrahedron Letters",

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T1 - Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine

AU - Lee, Baeck Kyoung

AU - Choi, Hwan Geun

AU - Roh, Eun Joo

AU - Lee, Won Koo

AU - Sim, Taebo

N1 - Funding Information: This research was supported by the Korea Institute of Science and Technology and a Grant (No. 2011-0028676 ) from the creative/challenging research program of the National Research Foundation of Korea funded by the Ministry of Education, Science and Technology , and a Grant (No.: A111345 ) of the Korea Health technology R&D Project, Ministry of Health & Welfare, Republic of Korea.

PY - 2013/2/6

Y1 - 2013/2/6

N2 - An efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (-)-8-epi-swainsonine.

AB - An efficient synthesis of (-)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (-)-8-epi-swainsonine.

KW - (-)-8-Epi-swainsonine

KW - Aziridine

KW - Indolizidine alkaloids

KW - Natural product

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84872018243&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.11.087

DO - 10.1016/j.tetlet.2012.11.087

M3 - Article

AN - SCOPUS:84872018243

SN - 0040-4039

VL - 54

SP - 553

EP - 556

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine

Abstract

Keywords

ASJC Scopus subject areas

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