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New chemical syntheses of cholest-4,6-dien-3-one

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Lipids

Abstract

Steroidal dienones represent a significant class of compounds that are useful intermediates in the further functionalization of the steroid nucleus. Their chemical synthesis can be problematic owing to the lack of a simplified method of preparation and the occurrence of impurities that can be difficult to remove. We have endeavored to develop new methods of chemical synthesis of cholest-4,6-dien-3-one that would yield a product of high purity.

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Abbreviations

Collindine:

2,4,6-trimethylpyridine

DBN:

1,5-diazabicyclo[4.3.0]non-5-ene

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

DDO:

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DMF:

dimethylformamide

NBS:

N-bromosuccinimide

PCC:

pyridinium chlorochromate

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Correspondence to Edward J. Parish.

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Parish, E.J., Sun, H., Lu, D. et al. New chemical syntheses of cholest-4,6-dien-3-one. Lipids 37, 1197–1200 (2002). https://doi.org/10.1007/s11745-002-1021-0

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  • DOI: https://doi.org/10.1007/s11745-002-1021-0

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