A short synthesis of (±)-oxetin

Thorsten Bach; Jürgen Schröder

doi:10.1002/jlac.199719971113

A short synthesis of (±)-oxetin

Thorsten Bach, Jürgen Schröder

Philipps-Universität Marburg

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

29 Scopus citations

Abstract

The antibiotic β-amino acid oxetin (rac-1) has been prepared by the stereoselective Paternò-Büchi reaction of enecarbamate 2 and n-butyl glyoxylate (5). The overall yield of the four-step synthesis is 14%. The order of the deprotection steps proved to be important in minimizing possible side reactions.

Original language	English
Pages (from-to)	2265-2267
Number of pages	3
Journal	Liebigs Annales
Issue number	11
DOIs	https://doi.org/10.1002/jlac.199719971113
State	Published - 1997
Externally published	Yes

Keywords

Amino acids
Antibiotics
Oxetanes
Photochemistry
Protective groups

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10.1002/jlac.199719971113

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title = "A short synthesis of (±)-oxetin",

abstract = "The antibiotic β-amino acid oxetin (rac-1) has been prepared by the stereoselective Patern{\`o}-B{\"u}chi reaction of enecarbamate 2 and n-butyl glyoxylate (5). The overall yield of the four-step synthesis is 14%. The order of the deprotection steps proved to be important in minimizing possible side reactions.",

keywords = "Amino acids, Antibiotics, Oxetanes, Photochemistry, Protective groups",

author = "Thorsten Bach and J{\"u}rgen Schr{\"o}der",

year = "1997",

doi = "10.1002/jlac.199719971113",

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journal = "Liebigs Annales",

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T1 - A short synthesis of (±)-oxetin

AU - Bach, Thorsten

AU - Schröder, Jürgen

PY - 1997

Y1 - 1997

N2 - The antibiotic β-amino acid oxetin (rac-1) has been prepared by the stereoselective Paternò-Büchi reaction of enecarbamate 2 and n-butyl glyoxylate (5). The overall yield of the four-step synthesis is 14%. The order of the deprotection steps proved to be important in minimizing possible side reactions.

AB - The antibiotic β-amino acid oxetin (rac-1) has been prepared by the stereoselective Paternò-Büchi reaction of enecarbamate 2 and n-butyl glyoxylate (5). The overall yield of the four-step synthesis is 14%. The order of the deprotection steps proved to be important in minimizing possible side reactions.

KW - Amino acids

KW - Antibiotics

KW - Oxetanes

KW - Photochemistry

KW - Protective groups

UR - http://www.scopus.com/inward/record.url?scp=33748718653&partnerID=8YFLogxK

U2 - 10.1002/jlac.199719971113

DO - 10.1002/jlac.199719971113

M3 - Article

AN - SCOPUS:33748718653

SN - 0947-3440

SP - 2265

EP - 2267

JO - Liebigs Annales

JF - Liebigs Annales

IS - 11

ER -

A short synthesis of (±)-oxetin

Abstract

Keywords

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