Stereoselective Preparation
of C1-C10 and C11-O14 Fragments of Narbonolide:
Exploiting the Versatility of Thiazolidinethione Chiral Auxiliary

C. Prasad Narasimhulu; Parthasarathi Das

doi:10.1055/s-0028-1083321

PAPER

Stereoselective Preparation of C1-C10 and C11-O14 Fragments of Narbonolide: Exploiting the Versatility of Thiazolidinethione Chiral Auxiliary [¹]

C. Prasad Narasimhulu, Parthasarathi Das*
Discovery Research, Dr. Reddy’s Laboratories Ltd., Bollaram Road, Miyapur, Hyderabad 500 049, India
Fax: +91(40)23045438; e-Mail: parthasarathi@drreddys.com; e-Mail: parthads@yahoo.com;

Abstract

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Abstract

An efficient stereoselective synthesis of the C1-C10 and C11-O14 fragments of narbonolide, have been accomplished by using a thiazolidinonethione as chiral auxiliary. The stereocenters at C2, C3, C4, C5, C8, and C9 in C1-C10 fragment and C12 and C13 in C11-C14 fragment were generated via asymmetric acyl-thiazolidinethione aldol reactions whereas the stereocenter at C6 was installed by means of Myers alkylation.

Key words

acyl-thiazolidinethione - aldol reaction - Crimmins protocol - Myers alkylation - Tebbe reaction

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References

1

DRL Publication No. 670.

2 Macrolide Antibiotics: Chemistry, Biology and Practice 2nd ed.: Omura S. Academic; San Diego: 2002.

3 Leclercq R. Clin. Infect. Dis. 2002, 34: 482

4a Agouridas C. Denis A. Auger J.-M. Benedetti Y. Bonnefoy A. Bretin F. Chantot J.-F. Dussarat A. Fromentin C. D’Ambrieres SG. Lachaud S. Laurin P. Le Martret O. Loyau V. Tessot N. J. Med. Chem. 1998, 41: 4080

4b Zhanel GG. Walters M. Noreddin A. Vercaigne LM. Wierzbowski A. Embil JM. Gin AS. Douthwaite S. Hoban DJ. Drugs 2002, 62: 12

5 Ma Z. Clark RF. Brazzale A. Wang S. Rupp MJ. Li L. Griesgraber G. Zhang S. Yong H. Phan LT. Nemoto PA. Chu DTW. Plattner JJ. Zhang X. Zhong P. Cao Z. Nilius AM. Shortridge VD. Flamm R. Mitten M. Meulbroek J. Ewing P. Alder J. Or YS. J. Med. Chem. 2001, 44: 4137

6a Denis A. Agouridas C. Auger J.-M. Benedetti Y. Bonnefoy A. Bretin F. Chantot J.-F. Dussarat A. Fromentin C. D’Ambrieres SG. Lachaud S. Laurin P. Le Martret O. Loyau V. Tessot N. Pejac J.-M. Perron S. Bioorg. Med. Chem. Lett. 1999, 9: 3075

6b Plata DJ. Leanna MR. Rasmussen M. McLaughlin MA. Condon SL. Kerdesky FAJ. King SA. Peterson MJ. Stoner EJ. Wittenberger SJ. ChemInform 2005, 36: 10

6c Henninger TC. Xu X. Abbanat D. Baum EZ. Foleno BD. Hilliard JJ. Bush K. Hlasta DJ. Macielag MJ. Bioorg. Med. Chem. Lett. 2004, 14: 4495

7a Hori T. Maezawa I. Nagahama N. Suzuki M. Chem. Commun. 1971, 304

7b Maezawa I. Hori T. Kinumaki A. Suzuki M. J. Antibiot. 1973, 26: 771

7c Xue Y. Zhao L. Liu H.-W. Sherman DH. Proc. Natl. Acad. Sci. U.S.A. 1998, 95: 12111

7d Xue Y. Sherman DH. Met. Eng. 2001, 3: 15

8a Kaiho T. Masamune S. Toyoda T. J. Org. Chem. 1982, 47: 1612

8b Venkatraman L. Aldrich CC. Sherman DH. Fecik RA. J. Org. Chem. 2005, 70: 7267

8c Venkatraman L. Salomon CE. Sherman DH. Fecik RA. J. Org. Chem. 2006, 71: 9853

9a Sai Baba V. Das P. Mukkanti K. Iqbal J. Tetrahedron Lett. 2006, 47: 6083

9b Sai Baba V. Das P. Mukkanti K. Iqbal J. Tetrahedron Lett. 2006, 47: 7927

9c Saibaba V. Sampath A. Mukkanti K. Iqbal J. Das P. Synthesis 2007, 2797

9d Das P. Saibaba V. Kirankumar C. Mahendar V. Synthesis 2008, 445

10 Narsimhulu CP. Iqbal J. Mukkanti K. Das P. Tetrahedron Lett. 2008, 49: 3185

11a Nagao Y. Yamada S. Kumagai T. Ochiai M. Fujita E. J. Chem. Soc., Chem. Commun. 1985, 1418

11b Nagao Y. Hagiwara Y. Kumagai T. Ochiai M. Inoue T. Hashimoto K. Fujita E. J. Org. Chem. 1986, 51: 2391

11c Romero-Ortega M. Colby DA. Olivo HF. Tetrahedron Lett. 2002, 43: 6439

12a Crimmins MT. Chaudhary K. Org. Lett. 2000, 2: 775

12b Crimmins MT. King BW. Tabet EA. Chaudhary K. J. Org. Chem. 2001, 66: 894

12c Crimmins MT. Christie HS. Chaudhary K. Long A. J. Am. Chem. Soc. 2005, 127: 13810

12d Crimmins MT. Caussanel F. J. Am. Chem. Soc. 2006, 128: 3128

13a Myers AG. Yang BH. Chen H. Gleason JL. J. Am. Chem. Soc. 1994, 116: 9361

13b Myers AG. McKinstry L. J. Am. Chem. Soc. 1996, 118: 2428

13c Myers AG. Yang BH. Chen H. McKinstry L. Kopecky DJ. Gleason JL. J. Am. Chem. Soc. 1997, 119: 6496

14 Myers AG. Yang BH. Kopecky DJ. Tetrahedron Lett. 1996, 37: 3623

15a Tebbe FN. Parshall GW. Reddy GS. J. Am. Chem. Soc. 1978, 100: 3611

15b Cuellar MA. Salas C. Cortes MJ. Morello A. Maya JD. Preite MD. Bioorg. Med. Chem. 2003, 11: 2489

16 Crossman JS. Perkins MV. J. Org. Chem. 2006, 71: 117