Synthesis of model ring systems related to C10-C18 analogues of the mycalamides/theopederins

John M. Gardiner; Richard Mills; Thomas Fessard

doi:10.1016/j.tetlet.2003.11.141

Synthesis of model ring systems related to C10-C18 analogues of the mycalamides/theopederins

John M. Gardiner, Richard Mills, Thomas Fessard

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

Abstract

Conjugate addition to D-galactose-derived pyranones 8 and 10, with in situ enolate alkylation, or protonation, provides pyranones 11-13 or 16-19. These are related to the C10-C18 fragment of the mycalamides and provide a short entry to C10, C11, C14 and C15 stereocentres. This approach is relevant to introduction of the side-chain and analogues thereof, and allows for variable C14 functionality. Two side-chain analogues, both C14 monomethylated diastereomers, the C14 unsubstituted system and the natural product-related C14 dimethyl functionality are prepared, and C13 epimeric functionality introduced. © 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1215-1217
Number of pages	2
Journal	Tetrahedron Letters
Volume	45
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2003.11.141
Publication status	Published - 2 Feb 2004

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10.1016/j.tetlet.2003.11.141

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title = "Synthesis of model ring systems related to C10-C18 analogues of the mycalamides/theopederins",

abstract = "Conjugate addition to D-galactose-derived pyranones 8 and 10, with in situ enolate alkylation, or protonation, provides pyranones 11-13 or 16-19. These are related to the C10-C18 fragment of the mycalamides and provide a short entry to C10, C11, C14 and C15 stereocentres. This approach is relevant to introduction of the side-chain and analogues thereof, and allows for variable C14 functionality. Two side-chain analogues, both C14 monomethylated diastereomers, the C14 unsubstituted system and the natural product-related C14 dimethyl functionality are prepared, and C13 epimeric functionality introduced. {\textcopyright} 2003 Elsevier Ltd. All rights reserved.",

author = "Gardiner, {John M.} and Richard Mills and Thomas Fessard",

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T1 - Synthesis of model ring systems related to C10-C18 analogues of the mycalamides/theopederins

AU - Gardiner, John M.

AU - Mills, Richard

AU - Fessard, Thomas

PY - 2004/2/2

Y1 - 2004/2/2

N2 - Conjugate addition to D-galactose-derived pyranones 8 and 10, with in situ enolate alkylation, or protonation, provides pyranones 11-13 or 16-19. These are related to the C10-C18 fragment of the mycalamides and provide a short entry to C10, C11, C14 and C15 stereocentres. This approach is relevant to introduction of the side-chain and analogues thereof, and allows for variable C14 functionality. Two side-chain analogues, both C14 monomethylated diastereomers, the C14 unsubstituted system and the natural product-related C14 dimethyl functionality are prepared, and C13 epimeric functionality introduced. © 2003 Elsevier Ltd. All rights reserved.

AB - Conjugate addition to D-galactose-derived pyranones 8 and 10, with in situ enolate alkylation, or protonation, provides pyranones 11-13 or 16-19. These are related to the C10-C18 fragment of the mycalamides and provide a short entry to C10, C11, C14 and C15 stereocentres. This approach is relevant to introduction of the side-chain and analogues thereof, and allows for variable C14 functionality. Two side-chain analogues, both C14 monomethylated diastereomers, the C14 unsubstituted system and the natural product-related C14 dimethyl functionality are prepared, and C13 epimeric functionality introduced. © 2003 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2003.11.141

DO - 10.1016/j.tetlet.2003.11.141

M3 - Article

SN - 1873-3581

VL - 45

SP - 1215

EP - 1217

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

Synthesis of model ring systems related to C10-C18 analogues of the mycalamides/theopederins

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