Convenient route to derivatives of the 2-deoxysugar subunits of the Kedarcidin chromophore: L-mycarose and L-kedarosamine

Martin J. Lear; Masahiro Hirama

doi:10.1016/S0040-4039(99)00906-5

Convenient route to derivatives of the 2-deoxysugar subunits of the Kedarcidin chromophore: L-mycarose and L-kedarosamine

Martin J. Lear, Masahiro Hirama

SCI - Chemistry

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

24 Citations (Scopus)

Abstract

An efficient and practical synthesis of mycarose and kedarosamine derivatives has been devised from ethyl (S)-lactate via a versatile (E)- alkene intermediate. Noteworthy transformations include a highly trans- selective one-pot Julia olefination protocol and intramolecular cyclisation of a 2,3-epoxy carbamate.

Original language	English
Pages (from-to)	4897-4900
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(99)00906-5
Publication status	Published - 1999 Jun 25

Keywords

Amino sugars
Cyclisation
Glycosides
Olefination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00906-5

Cite this

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abstract = "An efficient and practical synthesis of mycarose and kedarosamine derivatives has been devised from ethyl (S)-lactate via a versatile (E)- alkene intermediate. Noteworthy transformations include a highly trans- selective one-pot Julia olefination protocol and intramolecular cyclisation of a 2,3-epoxy carbamate.",

keywords = "Amino sugars, Cyclisation, Glycosides, Olefination",

author = "Lear, {Martin J.} and Masahiro Hirama",

note = "Funding Information: A Japanese Society for the Promotion of Science Fellowship (to M. J. L.) is gratefully acknowledged.",

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T2 - L-mycarose and L-kedarosamine

AU - Lear, Martin J.

AU - Hirama, Masahiro

N1 - Funding Information: A Japanese Society for the Promotion of Science Fellowship (to M. J. L.) is gratefully acknowledged.

PY - 1999/6/25

Y1 - 1999/6/25

N2 - An efficient and practical synthesis of mycarose and kedarosamine derivatives has been devised from ethyl (S)-lactate via a versatile (E)- alkene intermediate. Noteworthy transformations include a highly trans- selective one-pot Julia olefination protocol and intramolecular cyclisation of a 2,3-epoxy carbamate.

AB - An efficient and practical synthesis of mycarose and kedarosamine derivatives has been devised from ethyl (S)-lactate via a versatile (E)- alkene intermediate. Noteworthy transformations include a highly trans- selective one-pot Julia olefination protocol and intramolecular cyclisation of a 2,3-epoxy carbamate.

KW - Amino sugars

KW - Cyclisation

KW - Glycosides

KW - Olefination

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EP - 4900

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 26

ER -

Convenient route to derivatives of the 2-deoxysugar subunits of the Kedarcidin chromophore: L-mycarose and L-kedarosamine

Abstract

Keywords

ASJC Scopus subject areas

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