Asymmetric total synthesis of (+)-swainsonine

Soontorn Chooprayoon; Chutima Kuhakarn; Patoomratana Tuchinda; Vichai Reutrakul; Manat Pohmakotr

doi:10.1039/c0ob00388c

Asymmetric total synthesis of (+)-swainsonine

Soontorn Chooprayoon
, Chutima Kuhakarn
, Patoomratana Tuchinda
, Vichai Reutrakul
, Manat Pohmakotr

Mahidol University

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

34 Citations (Scopus)

Abstract

A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps.

Original language	English
Pages (from-to)	531-537
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	2
DOIs	https://doi.org/10.1039/c0ob00388c
Publication status	Published - 21 Jan 2011
Externally published	Yes

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10.1039/c0ob00388c

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title = "Asymmetric total synthesis of (+)-swainsonine",

abstract = "A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8\% overall yield in 10 steps.",

author = "Soontorn Chooprayoon and Chutima Kuhakarn and Patoomratana Tuchinda and Vichai Reutrakul and Manat Pohmakotr",

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AU - Chooprayoon, Soontorn

AU - Kuhakarn, Chutima

AU - Tuchinda, Patoomratana

AU - Reutrakul, Vichai

AU - Pohmakotr, Manat

PY - 2011/1/21

Y1 - 2011/1/21

N2 - A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps.

AB - A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps.

UR - https://www.scopus.com/pages/publications/78650732491

U2 - 10.1039/c0ob00388c

DO - 10.1039/c0ob00388c

M3 - Article

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VL - 9

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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ER -

Asymmetric total synthesis of (+)-swainsonine

Abstract

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