Acyl radical cyclizations in synthesis. Part 3. Synthesis of (±)-trans-3,5-bis-(t-butyldimethylsiloxy)-2-methylenecyclohexanone, an ‘A’ ring model for 1α, 25-dihydroxyvitamin D3

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19900002875 ◽

1990 ◽

pp. 2875-2879 ◽

Cited By ~ 21

Author(s):

Duncan Batty ◽

David Crich ◽

Simon M. Fortt

Keyword(s):

Radical Cyclizations ◽

Acyl Radical ◽

Dihydroxyvitamin D3 ◽

Ring Model

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ChemInform Abstract: Acyl Radical Cyclizations in Synthesis. Part 3. Synthesis of (.+-.)- trans-3,5-Bis(t-butyldimethylsiloxy)-2-methylenecyclohexanone, an “A” Ring Model for 1α,25-Dihydroxyvitamin D3.

ChemInform ◽

10.1002/chin.199107258 ◽

2010 ◽

Vol 22 (7) ◽

pp. no-no

Author(s):

D. BATTY ◽

D. CRICH ◽

S. M. FORTT

Keyword(s):

Radical Cyclizations ◽

Acyl Radical ◽

Dihydroxyvitamin D3 ◽

Ring Model

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Acyl radical cyclizations in synthesis. part 2 further substituent effects on the mode and efficiency of cyclizaion of 6-heptenoyl radicals.

Tetrahedron ◽

10.1016/s0040-4020(01)89779-9 ◽

1990 ◽

Vol 46 (6) ◽

pp. 2135-2148 ◽

Cited By ~ 32

Author(s):

David Crich ◽

K. Angeline Eustace ◽

Simon M. Fortt ◽

Timodthy J. Ritchie

Keyword(s):

Substituent Effects ◽

Radical Cyclizations ◽

Acyl Radical

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Synthesis of polyhydroxylated xanthones via acyl radical cyclizations

Tetrahedron Letters ◽

10.1016/j.tetlet.2011.10.153 ◽

2012 ◽

Vol 53 (2) ◽

pp. 111-114 ◽

Cited By ~ 6

Author(s):

George A. Kraus ◽

Feng Liu

Keyword(s):

Radical Cyclizations ◽

Acyl Radical

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ChemInform Abstract: Model Insect Antifeedants. Synthesis of Azadiradione Fragments Through Acyl Radical Cyclizations and Stannane Coupling Reactions.

ChemInform ◽

10.1002/chin.199629129 ◽

2010 ◽

Vol 27 (29) ◽

pp. no-no

Author(s):

A. FERNANDEZ-MATEOS ◽

G. P. COCA ◽

R. RUBIO GONZALES ◽

C. TAPIA HERNANDEZ

Keyword(s):

Radical Cyclizations ◽

Coupling Reactions ◽

Abstract Model ◽

Acyl Radical ◽

Insect Antifeedants

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ChemInform Abstract: An Iterative Approach to Biologically Important Fused Polycyclic Ethers via Acyl Radical Cyclizations.

ChemInform ◽

10.1002/chin.199649151 ◽

2010 ◽

Vol 27 (49) ◽

pp. no-no

Author(s):

P. A. EVANS ◽

J. D. ROSEMAN ◽

L. T. GARBER

Keyword(s):

Radical Cyclizations ◽

Iterative Approach ◽

Acyl Radical ◽

Polycyclic Ethers

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Synthesis of a 1α,25-dihydroxyvitamin D3A ring model by an acyl radical cyclization

Journal of the Chemical Society Chemical Communications ◽

10.1039/c39890001366 ◽

1989 ◽

Vol 0 (18) ◽

pp. 1366-1368 ◽

Cited By ~ 15

Author(s):

Duncan Batty ◽

David Crich ◽

Simon M. Fortt

Keyword(s):

Radical Cyclization ◽

Acyl Radical ◽

Ring Model

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Synthetic and Computational Studies of Acyl Radical Cyclizations with β-Alkoxyacrylates: Formal Synthesis of (±)-Longianone

Australian Journal of Chemistry ◽

10.1071/ch10462 ◽

2011 ◽

Vol 64 (4) ◽

pp. 409 ◽

Cited By ~ 8

Author(s):

Heather M. Aitken ◽

Carl H. Schiesser ◽

Christopher D. Donner

Keyword(s):

Density Functional ◽

Density Functional Theory Calculations ◽

Radical Cyclizations ◽

Computational Studies ◽

Fungal Metabolite ◽

Acyl Radical ◽

Functional Theory ◽

Formal Synthesis ◽

Acyl Radicals ◽

Insight Into

An investigation into the cyclization of acyl radicals with mono- and disubstituted β-alkoxyacrylates is described. Ether-tethered acyl radicals, generated directly from the corresponding aldehyde, undergo cyclization to form dioxaspiro heterocyclic systems including 1,7-dioxaspiro[4,4]nonane-4,8-dione and 1,8-dioxaspiro[5,4]decane-5,9-dione. This strategy is applied to a concise formal synthesis of the fungal metabolite longianone. Density functional theory calculations provide insight into the chemistry of the acyl radicals in this study.

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