A facile and efficient synthesis of (+)- and (-)-allo-muscarine and analogs

Jens Chr. Norrild; Christian Pedersen

doi:10.1055/s-1997-1323

A facile and efficient synthesis of (+)- and (-)-allo-muscarine and analogs

Jens Chr. Norrild, Christian Pedersen

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Treatment of easily obtainable 1-alkylamino-1,3,6-trideoxyhexitols with hydrogen fluoride in the presence of formic acid gives the corresponding C-5 inverted 2,5-anhydrides in high yields. The synthesis of allo-muscarine and its N-benzyl analog from galactono-1,4-lactone is reported in 30 and 41% overall yield, respectively.

Original language	English
Journal	Synthesis
Issue number	10
Pages (from-to)	1128-1130
ISSN	0039-7881
DOIs	https://doi.org/10.1055/s-1997-1323
Publication status	Published - 1997

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title = "A facile and efficient synthesis of (+)- and (-)-allo-muscarine and analogs",

abstract = "Treatment of easily obtainable 1-alkylamino-1,3,6-trideoxyhexitols with hydrogen fluoride in the presence of formic acid gives the corresponding C-5 inverted 2,5-anhydrides in high yields. The synthesis of allo-muscarine and its N-benzyl analog from galactono-1,4-lactone is reported in 30 and 41% overall yield, respectively.",

author = "Norrild, {Jens Chr.} and Christian Pedersen",

year = "1997",

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journal = "Synthesis",

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T1 - A facile and efficient synthesis of (+)- and (-)-allo-muscarine and analogs

AU - Norrild, Jens Chr.

AU - Pedersen, Christian

PY - 1997

Y1 - 1997

N2 - Treatment of easily obtainable 1-alkylamino-1,3,6-trideoxyhexitols with hydrogen fluoride in the presence of formic acid gives the corresponding C-5 inverted 2,5-anhydrides in high yields. The synthesis of allo-muscarine and its N-benzyl analog from galactono-1,4-lactone is reported in 30 and 41% overall yield, respectively.

AB - Treatment of easily obtainable 1-alkylamino-1,3,6-trideoxyhexitols with hydrogen fluoride in the presence of formic acid gives the corresponding C-5 inverted 2,5-anhydrides in high yields. The synthesis of allo-muscarine and its N-benzyl analog from galactono-1,4-lactone is reported in 30 and 41% overall yield, respectively.

U2 - 10.1055/s-1997-1323

DO - 10.1055/s-1997-1323

M3 - Journal article

SN - 0039-7881

SP - 1128

EP - 1130

JO - Synthesis

JF - Synthesis

IS - 10

ER -

A facile and efficient synthesis of (+)- and (-)-allo-muscarine and analogs

Abstract

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