A short and efficient synthesis of (2S,3S,4S)-tert-butyl 3,4-dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

Mikko Passiniemi; Ari M.P. Koskinen

doi:10.1055/s-0029-1218843

A short and efficient synthesis of (2S,3S,4S)-tert-butyl 3,4-dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

Mikko Passiniemi, Ari M.P. Koskinen

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

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Abstract

Asymmetric synthesis of the title compound was accomplished starting from L-serine. Stannoxane-mediated lactamization provided the key intermediate in good yield.

Original language	English
Pages (from-to)	2816-2822
Journal	SYNTHESIS: STUTTGART
Issue number	16
DOIs	https://doi.org/10.1055/s-0029-1218843
Publication status	Published - 2010
MoE publication type	A1 Journal article-refereed

Keywords

natural products
stereoselective synthesis
olefination
alpha,beta-unsaturated lactam
dihydroxylation

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10.1055/s-0029-1218843

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title = "A short and efficient synthesis of (2S,3S,4S)-tert-butyl 3,4-dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate",

abstract = "Asymmetric synthesis of the title compound was accomplished starting from L-serine. Stannoxane-mediated lactamization provided the key intermediate in good yield.",

keywords = "natural products, stereoselective synthesis, olefination, alpha,beta-unsaturated lactam, dihydroxylation",

author = "Mikko Passiniemi and Koskinen, {Ari M.P.}",

year = "2010",

doi = "10.1055/s-0029-1218843",

language = "English",

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journal = "SYNTHESIS: STUTTGART",

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publisher = "Georg Thieme Verlag",

number = "16",

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T1 - A short and efficient synthesis of (2S,3S,4S)-tert-butyl 3,4-dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

AU - Passiniemi, Mikko

AU - Koskinen, Ari M.P.

PY - 2010

Y1 - 2010

N2 - Asymmetric synthesis of the title compound was accomplished starting from L-serine. Stannoxane-mediated lactamization provided the key intermediate in good yield.

AB - Asymmetric synthesis of the title compound was accomplished starting from L-serine. Stannoxane-mediated lactamization provided the key intermediate in good yield.

KW - natural products

KW - stereoselective synthesis

KW - olefination

KW - alpha,beta-unsaturated lactam

KW - dihydroxylation

U2 - 10.1055/s-0029-1218843

DO - 10.1055/s-0029-1218843

M3 - Article

SN - 0039-7881

SP - 2816

EP - 2822

JO - SYNTHESIS: STUTTGART

JF - SYNTHESIS: STUTTGART

IS - 16

ER -

A short and efficient synthesis of (2S,3S,4S)-tert-butyl 3,4-dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

Abstract

Keywords

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