Synthesis of Conformationally Restricted Symmetric Macrodiolides via Carbonyl Ylides

Sengodagounder Muthusamy; Manickasamy Sivaguru; Eringathodi Suresh

doi:10.1055/s-0033-1338801

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(14): 2034-2042
DOI: 10.1055/s-0033-1338801

paper

Synthesis of Conformationally Restricted Symmetric Macrodiolides via Carbonyl Ylides

Sengodagounder Muthusamy*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620024, India Fax: +91(431)2407045 eMail: muthu@bdu.ac.in

,

Manickasamy Sivaguru

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620024, India Fax: +91(431)2407045 eMail: muthu@bdu.ac.in

,

Eringathodi Suresh

^bCentral Salt & Marine Chemicals Research Institute, Bhavnagar 364002, India

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

This paper is dedicated with best wishes to Professor Goverdhan Mehta on the occasion of his 70^th birthday.

Abstract

Reaction of bis-diazocarbonyl compounds and dicarbaldehyde/divinyl derivatives in the presence of rhodium(II) acetate dimer as the catalyst led to the facile synthesis of conformationally restricted symmetric macrodiolides incorporating oxa/dioxa-bridged bicyclic systems. The structure and configuration of a representative macrodiolide were unequivocally confirmed using single-crystal X-ray analysis.

Key words

cycloaddition - diazo compounds - macrocycles - rhodium - ylides

Volltext

Referenzen

References

1a Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides. Wiley-Interscience; New York: 1998
1b Regitz M, Mass G. Diazo Compounds: Properties and Synthesis. Academic; New York: 1986
1c Zhang Z, Wang J. Tetrahedron 2008; 64: 6577

2a Hodgson DM, Labande AH, Muthusamy S. Org. React. 2013; 80: 133
2b Mehta G, Muthusamy S. Tetrahedron 2002; 58: 9477
2c Padwa A, Weingarten MD. Chem. Rev. 1996; 96: 223

3 Padwa A. Tetrahedron 2011; 67: 8052 ; and references cited therein

4a Kang EJ, Lee E. Chem. Rev. 2005; 105: 4348
4b Gerbino DC, Scoccia J, Koll LC, Mandolesi SD, Podesta JC. Organometallics 2012; 31: 662
4c Salunke GB, Shivakumar I, Gurjar MK. Tetrahedron Lett. 2009; 50: 2048

5a Takahashi S, Souma K, Hashimoto R, Koshino H, Nakata T. J. Org. Chem. 2004; 69: 4509
5b Metz P. Top. Curr. Chem. 2005; 244: 215

6a Driggers EM, Hale SP, Jinbo Lee J, Terrett NK. Nat. Rev. Drug Discovery 2007; 7: 608
6b Marsault E, Peterson ML. J. Med. Chem. 2011; 54: 1961

7 Veber DF, Johnson SR, Cheng H.-Y, Smith BR, Ward KW, Kopple KD. J. Med. Chem. 2002; 45: 2615

8a Muthusamy S, Gnanaprakasam B, Suresh E. Org. Lett. 2005; 7: 4577
8b Muthusamy S, Krishnamurthi J, Nethaji M. Chem. Commun. 2005; 3862
8c Muthusamy S, Gnanaprakasam B. Tetrahedron 2005; 61: 1309
8d Muthusamy S, Babu SA, Gunanathan C, Ganguly B, Suresh E, Dastidar P. J. Org. Chem. 2002; 67: 8019
8e Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P, Jasra RV. Tetrahedron 2001; 57: 7009

9a Muthusamy S, Gnanaprakasam B, Suresh E. Org. Lett. 2006; 8: 1913
9b Muthusamy S, Gnanaprakasam B. Tetrahedron 2007; 63: 3355
9c Muthusamy S, Srinivasan P. Tetrahedron Lett. 2009; 50: 3794
9d Muthusamy S, Karikalan T, Suresh E. Tetrahedron Lett. 2011; 52: 1934

10 Mottet C, Hamelin O, Garavel G, Deprés J.-P, Greene AE. J. Org. Chem. 1999; 64: 1380
11 Pollet P, Gelin S. Synthesis 1978; 142
12 Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P, Jasra RV. Tetrahedron 2000; 56: 6307
13 Muthusamy S, Babu SA, Gunanathan C. Tetrahedron Lett. 2002; 43: 3931
14 CCDC-900352 (for 10a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

Zusatzmaterial

Supporting Information