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

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2009.06.063

Cite this

@article{2d3e845ee85f41b0a61088a539abd038,

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. ",

year = "2009",

month = aug,

day = "15",

doi = "10.1016/j.tet.2009.06.063",

language = "English (US)",

volume = "65",

pages = "6739--6745",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "33",

}

TY - JOUR

T1 - A nature-inspired Diels-Alder reaction facilitates construction of the bicyclo[2.2.2]octane core of andibenin B

AU - Spangler, Jillian E.

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.

PY - 2009/8/15

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.

UR - https://www.scopus.com/pages/publications/67650215078

UR - https://www.scopus.com/inward/citedby.url?scp=67650215078&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2009.06.063

DO - 10.1016/j.tet.2009.06.063

M3 - Article

C2 - 21687810

AN - SCOPUS:67650215078

SN - 0040-4020

VL - 65

SP - 6739

EP - 6745

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this