RE: ORGLIST:What is the Abramov reaction???

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From: Ismail F (F.M.Ismail$##$livjm.ac.uk)
Date: Wed Jul 24 2002 - 07:34:10 EDT


24. July 2002
 
Dear Dr Regla,
 
I presume you are referring to the Diels Alder/Retro Diels Alder study
between "cyclones" and ethenes. See:
 
Addition of Ethylenic Compounds to Tetracyclones
C. F. H. ALLEN, R. W. RYAN , Jr., J. A. VanALLAN;
J. Org. Chem.; 1962; 27(3); 778-779.
 
However there is an "Abramov reaction" used in the synthesis of phostone
sugars. It involves reaction of sugar aldehydes and di- or trialkyl
phosphites which undergo subsequent intramolecular transesterification:
 
See references lists 4 & 5given by Stoianova & Hanson in their latest paper:

 
A Ring-Closing Metathesis Strategy to Phosphonosugars
Stoianova, D. S.; Hanson, P. R.;
Org. Lett.; (Communication); 2001; 3(21); 3285-3288.
 
ol016491pb00004 4. (a) Hanessian, S.; Rogel, O. J. Org. Chem. 2000, 65,
2667-2674.
(b) Hanessian, S.; Rogel, O. Bioorg. Med. Chem. Lett. 1999, 9, 2441-2446.
 (c) Harvey, T. C.; Simiand, C.; Weiler, L.; Withers, S. G. J. Org. Chem.
1997, 62, 6722-6725.
(d) Darrow, J. W.; Drueckhammer, D. G. Bioorg. Med. Chem. 1996, 4,
1341-1348.
(e) Hanessian, S.; Galeotti, N.; Rosen, P.; Oliva, G.; Babu, S. Bioorg. Med.
Chem. Lett. 1994, 4, 2763-2768.
(f) Darrow, J. W.; Drueckhammer, D. G. J. Org. Chem. 1994, 59, 2976-2985.
(g) Molin, H.; Noren, J. O.; Claesson, A. Carbohydr. Res. 1989, 194,
209-221.
(h) Wroblewski, A. E. Tetrahedron 1986, 42, 3595-3606. (i) Thiem, J.;
Gunther, M.; Paulsen, H.; Kopf, J. Chem. Ber. 1977, 110, 3190-3200.
(j) Engel, R. Handbook of Organo-phosphorus Chemistry; Marcel Dekker: New
York, 1992.
ol016491pb000055. For some recent examples of the synthesis of
non-functionalized cyclic phosphonates, see:
(a) Tasz, M. K.; Rodriguez, O. P.; Cremer, S. E.; Hussain, M. S.; Haque, M.
J. Chem. Soc., Perkin Trans. 2 1996, 2221-2226.
(b) Yokomatsu, T.; Shioya, Y.; Iwasawa, H.; Shibuya, S. Heterocycles 1997,
46, 463-472. (c) Brel, V. K. Synthesis 1998, 710-712.
 
Results found using the superlative ACS search engine at:
http://pubs.acs.org/journals/query/subscriberSearch.jsp
<http://pubs.acs.org/journals/query/subscriberSearch.jsp>
 
If you can afford it, online subscription to ACS and journals and their
excellent archive may prove invaluable.
 
Best Wishes
 
F.M.Ismail$##$livjm.ac.uk <mailto:F.M.Ismail$##$livjm.ac.uk>
http://www.staff.livjm.ac.uk/pacfisma/
<http://www.staff.livjm.ac.uk/pacfisma/>
 
____________________________________________________________________________
____________________
 
Dr Fyaz MD Ismail

Senior Lecturer in Medicinal Chemistry

The Medicinal Chemistry Research Group
The School of Pharmacy and
<http://www.staff.livjm.ac.uk/capbnich/chemistry/chemistry.htm> Chemistry
Liverpool John Moores University
Room 221C James Parsons Building
Byrom Street
Liverpool L3 3AF

Telephone: +44 (0)151 231 2231.

____________________________________________________________________________
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-----Original Message-----
From: antonio regla [mailto:areglac$##$yahoo.com]
Sent: 24 July 2002 02:26
To: everybody$##$orglist.net
Subject: ORGLIST:What is the Abramov reaction???

Dear list members:

Does anyone know what is the Abramov or the Retro-Abramov reaction?? I have
looked it up in name reaction sites in the internet, and haven't been able
to find it. I've also checked two books on name reactions, and there's no
mention of it, the same with one of the editions of the Merck Index that had
a section on name reactions. I would appreciate if anyone can provide a
reference on this reaction, I believe it deals with some phosphorus
compounds. I would appreciate any help you can give me.

Sincerely,

Antonio Regla

Facultad de Farmacia

Universidad Autonoma del Estado de Morelos

Cuernavaca, Mexico

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