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Synlett 2007(12): 1881-1884
DOI: 10.1055/s-2007-984521
DOI: 10.1055/s-2007-984521
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of the Core Structure of the Cyclocitrinols via SmI2-Mediated Fragmentation of a Cyclopropane Precursor
Further Information
Received
26 April 2007
Publication Date:
25 June 2007 (online)
Publication History
Publication Date:
25 June 2007 (online)
![](https://www.thieme-connect.de/media/synlett/200712/lookinside/thumbnails/10.1055-s-2007-984521-1.jpg)
Abstract
The first synthetic entry towards the cyclocitrinols, a new class of natural products possessing a steroid-analogue structure with a characteristic bicyclo[4.4.1]undecane AB ring system, was elaborated. In the key step, a cyclopropanated intermediate (prepared from dehydroepiandrosterone) was subjected to reductive fragmentation (using SmI2 in THF).
Key words
steroids - samarium diiodide - stereoselective synthesis - fragmentation - natural products
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Amagata T.Amagata A.Tenney K.Valeriote FA.Lobkovsky E.Clardy J.Crews P. Org. Lett. 2003, 5: 4393 - 2
Kozlovsky AG.Zhelifonova VP.Ozerskaya SM.Vinokurova NG.Adanin VM.Gräfe U. Pharmazie 2000, 55: 470 - 3
Marinho AMD.Rodrigues-Filho E.Ferreira AG.Santos LS. J. Braz. Chem. Soc. 2005, 16: 1342 - Other prominent examples for compounds with a bicyclo[4.4.1]undecane ring system are:
-
4a Spiniferin:
Cimino G.De Stefano S.Minale L.Trivellone E. Tetrahedron Lett. 1975, 3727 -
4b E. Vogel’s 1,6-methano[10]annulene:
Vogel E.Roth HD. Angew. Chem. 1964, 76: 145 - 5
El Sheikh S.Kausch N.Schmalz H.-G. Synlett 2006, 1527 - 6
Sucrow W.Howard S. Chem. Ber. 1985, 118: 4341 - 7
Tadanier J. J. Org. Chem. 1966, 31: 2124 - 8
Turner AB.Ringold HJ. J. Chem. Soc. C 1967, 1720 - 9
Sharpless KB.Lauer RF.Teranishi AY. J. Am. Chem. Soc. 1973, 95: 6137 - 10
Mukaiyama T.Matsuo J.Kitagawa H. Chem. Lett. 2000, 11: 1250 - 11
Ito Y.Hirao T.Saegusa T. J. Org. Chem. 1978, 43: 1011 - 12
Nicolaou KC.Montagnon T.Baran PS. Angew. Chem. Int. Ed. 2002, 41: 993 - 13
Gamoh K.Hirayama M.Ikekawa N. J. Chem. Soc., Perkin Trans. 1 1984, 449 - 14
Heusler K.Kalvoda J. Angew. Chem., Int. Ed. Engl. 1964, 3: 525 - 15
Kirk DN.Rajagopalan MS.Varley MJ. J. Chem. Soc., Perkin Trans. 1 1983, 2225