Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones

Jared T. Hammill; Julia Contreras-García; Aaron M. Virshup; David N. Beratan; Weitao Yang; Peter Wipf

doi:10.1016/j.tet.2010.04.112

Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones

Jared T. Hammill
, Julia Contreras-García
, Aaron M. Virshup
, David N. Beratan
, Weitao Yang
, Peter Wipf

Pharmaceutical Sciences

Producción científica: Article › revisión exhaustiva

14 Citas (Scopus)

Resumen

Functionalized bicyclo[3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57-88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR studies supported the mechanistic hypothesis. The bicyclic ring products occupy novel chemical space according to ChemGPS and Chemaxon chemical diversity and cheminformatics analyses.

Idioma original	English
Páginas (desde-hasta)	5852-5862
Número de páginas	11
Publicación	Tetrahedron
Volumen	66
N.º	31
DOI	https://doi.org/10.1016/j.tet.2010.04.112
Estado	Published - jul 31 2010

Nota bibliográfica

Funding Information:
The authors thank Dr. Steven Geib (University of Pittsburgh) for the X-ray structure analyses of 14 and 20 , and NIH/NIGMS (P41GM081275; P50GM067082) for financial support.

Financiación

The authors thank Dr. Steven Geib (University of Pittsburgh) for the X-ray structure analyses of 14 and 20 , and NIH/NIGMS (P41GM081275; P50GM067082) for financial support.

Financiadores	Número del financiador
National Institutes of Health (NIH)
National Institute of General Medical Sciences	P50GM067082, P41GM081275

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.04.112

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title = "Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones",

abstract = "Functionalized bicyclo[3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57-88\%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR studies supported the mechanistic hypothesis. The bicyclic ring products occupy novel chemical space according to ChemGPS and Chemaxon chemical diversity and cheminformatics analyses.",

keywords = "Bicyclo[3.3.1]nonenones, Chemical diversity analysis, Epoxyketone rearrangement, Ring-opening",

author = "Hammill, \{Jared T.\} and Julia Contreras-Garc{\'i}a and Virshup, \{Aaron M.\} and Beratan, \{David N.\} and Weitao Yang and Peter Wipf",

note = "Funding Information: The authors thank Dr. Steven Geib (University of Pittsburgh) for the X-ray structure analyses of 14 and 20 , and NIH/NIGMS (P41GM081275; P50GM067082) for financial support. ",

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month = jul,

day = "31",

doi = "10.1016/j.tet.2010.04.112",

language = "English",

volume = "66",

pages = "5852--5862",

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T1 - Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones

AU - Hammill, Jared T.

AU - Contreras-García, Julia

AU - Virshup, Aaron M.

AU - Beratan, David N.

AU - Yang, Weitao

AU - Wipf, Peter

N1 - Funding Information: The authors thank Dr. Steven Geib (University of Pittsburgh) for the X-ray structure analyses of 14 and 20 , and NIH/NIGMS (P41GM081275; P50GM067082) for financial support.

PY - 2010/7/31

Y1 - 2010/7/31

N2 - Functionalized bicyclo[3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57-88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR studies supported the mechanistic hypothesis. The bicyclic ring products occupy novel chemical space according to ChemGPS and Chemaxon chemical diversity and cheminformatics analyses.

AB - Functionalized bicyclo[3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57-88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR studies supported the mechanistic hypothesis. The bicyclic ring products occupy novel chemical space according to ChemGPS and Chemaxon chemical diversity and cheminformatics analyses.

KW - Bicyclo[3.3.1]nonenones

KW - Chemical diversity analysis

KW - Epoxyketone rearrangement

KW - Ring-opening

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UR - https://www.scopus.com/pages/publications/77955471052#tab=citedBy

U2 - 10.1016/j.tet.2010.04.112

DO - 10.1016/j.tet.2010.04.112

M3 - Article

AN - SCOPUS:77955471052

SN - 0040-4020

VL - 66

SP - 5852

EP - 5862

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

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