6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction.

6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. Research Abstract Details 

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6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. Abstract Text:

Thomas J Greshock,Raymond L Funk,

6-Bromomethyl-4H-1,3-dioxin has been prepared in three steps from allyl iodide. A variety of enolates were then alkylated with this bromide. The resulting 6-alkyl-4H-1,3-dioxins were either subjected to further multistep transformations and/or heated to effect facile retrocycloaddition reactions. The resulting enones smoothly participated in novel endo-conjugate addition reactions with both carbon and nitrogen nucleophiles. For example, several bicyclo[4.3.1]decan-3,10-diones, the carbon framework of the CP compounds, were constructed using this novel annulation strategy. In another natural product study, a benzazocine related to the heterocyclic framework of the ring-opened tautomeric form of FR-900482 was also prepared using this methodology. Finally, a piperidin-4-one obtained from a 6-endo conjugate addition was converted to the naturally occurring (2S,4R)-4-hydroxypipecolic acid. Collectively, these examples document the synthetic equivalency of dioxin 1 with bromomethyl vinyl ketone and, moreover, delineate a strategy for accomplishing the sequential reactions with nucleophiles at the alpha' followed by the beta electrophilic sites.

6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. Publishing Authors By Initials

TJ Greshock,RL Funk,

For similar organic chemicals: hydrocarbons: hydrocarbons, cyclic research abstracts see: organic chemicals: hydrocarbons: hydrocarbons, cyclic research

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6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 124

Page Numbers: 754-5

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 6

MONTH: Feb

YEAR: 2002

6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. Keywords Mesh Terms:

KEYWORDS: Hydrocarbons, Cyclic

MESH TERMS: chemical synthesis

Chemical & Substance for Abstract: 6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. Information

Substance Name: Hydrocarbons, Cyclic

Registry Number: 0

Grant and Affiliation Information for 6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction.

AFFILIATION: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM28663

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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