trans-acetonide controlled endo-selective intramolecular nitrone-alkene cycloaddition of hept-6-enoses: A facile entry to calystegines, tropanes, and hydroxylated aminocycloheptanes

Tony K.M. Shing; Wai F. Wong; Taketo Ikeno; Tohru Yamada

doi:10.1021/ol062621o

trans-acetonide controlled endo-selective intramolecular nitrone-alkene cycloaddition of hept-6-enoses: A facile entry to calystegines, tropanes, and hydroxylated aminocycloheptanes

Tony K.M. Shing, Wai F. Wong, Taketo Ikeno, Tohru Yamada

Department of Chemistry

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

45 Citations (Scopus)

Abstract

(Chemical Equation Presented) High-yielding endo-selective intramolecular nitrone-alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.

Original language	English
Pages (from-to)	207-209
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	2
DOIs	https://doi.org/10.1021/ol062621o
Publication status	Published - 2007 Jan 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol062621o

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abstract = "(Chemical Equation Presented) High-yielding endo-selective intramolecular nitrone-alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.",

author = "Shing, {Tony K.M.} and Wong, {Wai F.} and Taketo Ikeno and Tohru Yamada",

year = "2007",

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T2 - A facile entry to calystegines, tropanes, and hydroxylated aminocycloheptanes

AU - Shing, Tony K.M.

AU - Wong, Wai F.

AU - Ikeno, Taketo

AU - Yamada, Tohru

PY - 2007/1/18

Y1 - 2007/1/18

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trans-acetonide controlled endo-selective intramolecular nitrone-alkene cycloaddition of hept-6-enoses: A facile entry to calystegines, tropanes, and hydroxylated aminocycloheptanes

Abstract

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