Synthesis of a C(4)-C(9) eleutheside template from D-glucal

Kolbot By; Patrick A. Kelly; Mark J. Kurth; Marilyn M. Olmstead; Michael H. Nantz

doi:10.1016/S0040-4020(00)01117-0

Synthesis of a C(4)-C(9) eleutheside template from D-glucal

Kolbot By, Patrick A. Kelly, Mark J. Kurth, Marilyn M. Olmstead, Michael H. Nantz

Chemistry

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

12 Scopus citations

Abstract

D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH₄ in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses.

Original language	English (US)
Pages (from-to)	1183-1187
Number of pages	5
Journal	Tetrahedron
Volume	57
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4020(00)01117-0
State	Published - Feb 11 2001

Keywords

D-glucal
Eleutheside
Epoxide
Hexenulose
Stereoselective

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "Synthesis of a C(4)-C(9) eleutheside template from D-glucal",

abstract = "D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses.",

keywords = "D-glucal, Eleutheside, Epoxide, Hexenulose, Stereoselective",

author = "Kolbot By and Kelly, {Patrick A.} and Kurth, {Mark J.} and Olmstead, {Marilyn M.} and Nantz, {Michael H.}",

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T1 - Synthesis of a C(4)-C(9) eleutheside template from D-glucal

AU - By, Kolbot

AU - Kelly, Patrick A.

AU - Kurth, Mark J.

AU - Olmstead, Marilyn M.

AU - Nantz, Michael H.

PY - 2001/2/11

Y1 - 2001/2/11

N2 - D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses.

AB - D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses.

KW - D-glucal

KW - Eleutheside

KW - Epoxide

KW - Hexenulose

KW - Stereoselective

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U2 - 10.1016/S0040-4020(00)01117-0

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EP - 1187

JO - Tetrahedron

JF - Tetrahedron

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