Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides

James R. Donald; Michael G. Edwards; Richard J. K. Taylor

doi:10.1016/j.tetlet.2007.05.145

Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides

James R. Donald, Michael G. Edwards, Richard J. K. Taylor

Chemistry

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

Abstract

A mild and straightforward method for the preparation of 4H-5,6-dihydro-1,2-oxazines from keto-epoxides via cyclisation of the intermediate oximes is reported, as is a preparative route to 3-amino-7,8-dimethoxychromen-2-one; these procedures were then employed to prepare a novel analogue of trichodermamide natural products. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5201-5204
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2007.05.145
Publication status	Published - 23 Jul 2007

Keywords

X=Y-ZH SYSTEMS
POTENTIAL 1,3-DIPOLES
CYCLOADDITION
STEREOSELECTIVITY
REARRANGEMENT
DERIVATIVES
DIPEPTIDES
NITRONES
STRAIN

Access to Document

10.1016/j.tetlet.2007.05.145

Cite this

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title = "Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides",

abstract = "A mild and straightforward method for the preparation of 4H-5,6-dihydro-1,2-oxazines from keto-epoxides via cyclisation of the intermediate oximes is reported, as is a preparative route to 3-amino-7,8-dimethoxychromen-2-one; these procedures were then employed to prepare a novel analogue of trichodermamide natural products. (c) 2007 Elsevier Ltd. All rights reserved.",

keywords = "X=Y-ZH SYSTEMS, POTENTIAL 1,3-DIPOLES, CYCLOADDITION, STEREOSELECTIVITY, REARRANGEMENT, DERIVATIVES, DIPEPTIDES, NITRONES, STRAIN",

author = "Donald, {James R.} and Edwards, {Michael G.} and Taylor, {Richard J. K.}",

year = "2007",

month = jul,

day = "23",

doi = "10.1016/j.tetlet.2007.05.145",

language = "English",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "30",

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TY - JOUR

T1 - Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides

AU - Donald, James R.

AU - Edwards, Michael G.

AU - Taylor, Richard J. K.

PY - 2007/7/23

Y1 - 2007/7/23

N2 - A mild and straightforward method for the preparation of 4H-5,6-dihydro-1,2-oxazines from keto-epoxides via cyclisation of the intermediate oximes is reported, as is a preparative route to 3-amino-7,8-dimethoxychromen-2-one; these procedures were then employed to prepare a novel analogue of trichodermamide natural products. (c) 2007 Elsevier Ltd. All rights reserved.

AB - A mild and straightforward method for the preparation of 4H-5,6-dihydro-1,2-oxazines from keto-epoxides via cyclisation of the intermediate oximes is reported, as is a preparative route to 3-amino-7,8-dimethoxychromen-2-one; these procedures were then employed to prepare a novel analogue of trichodermamide natural products. (c) 2007 Elsevier Ltd. All rights reserved.

KW - X=Y-ZH SYSTEMS

KW - POTENTIAL 1,3-DIPOLES

KW - CYCLOADDITION

KW - STEREOSELECTIVITY

KW - REARRANGEMENT

KW - DERIVATIVES

KW - DIPEPTIDES

KW - NITRONES

KW - STRAIN

U2 - 10.1016/j.tetlet.2007.05.145

DO - 10.1016/j.tetlet.2007.05.145

M3 - Article

SN - 0040-4039

VL - 48

SP - 5201

EP - 5204

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -