A nature-inspired Diels-Alder reaction facilitates construction of the bicyclo[2.2.2]octane core of andibenin B

Jillian E. Spangler; Erik J. Sorensen

doi:10.1016/j.tet.2009.06.063

A nature-inspired Diels-Alder reaction facilitates construction of the bicyclo[2.2.2]octane core of andibenin B

Jillian E. Spangler, Erik J. Sorensen

Chemistry

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

20 Scopus citations

Abstract

A rapid synthesis of the bicyclo[2.2.2]octane core of andibenin B via a nature-inspired intramolecular [4+2] cycloaddition is described. This cycloaddition permits the construction of a sterically congested bicycle and simultaneously establishes three new all-carbon quaternary stereogenic centers in a highly efficient fashion.

Original language	English (US)
Pages (from-to)	6739-6745
Number of pages	7
Journal	Tetrahedron
Volume	65
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2009.06.063
State	Published - Aug 15 2009

All Science Journal Classification (ASJC) codes

Drug Discovery
Biochemistry
Organic Chemistry

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10.1016/j.tet.2009.06.063

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title = "A nature-inspired Diels-Alder reaction facilitates construction of the bicyclo[2.2.2]octane core of andibenin B",

abstract = "A rapid synthesis of the bicyclo[2.2.2]octane core of andibenin B via a nature-inspired intramolecular [4+2] cycloaddition is described. This cycloaddition permits the construction of a sterically congested bicycle and simultaneously establishes three new all-carbon quaternary stereogenic centers in a highly efficient fashion.",

author = "Spangler, {Jillian E.} and Sorensen, {Erik J.}",

note = "Funding Information: We gratefully acknowledge NIGMS (GM065483), Princeton University, the Merck Research Laboratories, and Boehringer-Ingelheim, and a predoctoral fellowship from the National Science Foundation (J.E.S.) for supporting this work. ",

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AU - Sorensen, Erik J.

N1 - Funding Information: We gratefully acknowledge NIGMS (GM065483), Princeton University, the Merck Research Laboratories, and Boehringer-Ingelheim, and a predoctoral fellowship from the National Science Foundation (J.E.S.) for supporting this work.

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Y1 - 2009/8/15

N2 - A rapid synthesis of the bicyclo[2.2.2]octane core of andibenin B via a nature-inspired intramolecular [4+2] cycloaddition is described. This cycloaddition permits the construction of a sterically congested bicycle and simultaneously establishes three new all-carbon quaternary stereogenic centers in a highly efficient fashion.

AB - A rapid synthesis of the bicyclo[2.2.2]octane core of andibenin B via a nature-inspired intramolecular [4+2] cycloaddition is described. This cycloaddition permits the construction of a sterically congested bicycle and simultaneously establishes three new all-carbon quaternary stereogenic centers in a highly efficient fashion.

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A nature-inspired Diels-Alder reaction facilitates construction of the bicyclo[2.2.2]octane core of andibenin B

Abstract

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