Facile Stereoselective Synthesis of the C12-C24 Fragment of Macrolactin-A

Abstract

A simple and efficient stereoselective synthesis of the C12-C24 fragment of the natural product macrolactin-A was achieved from d-glucose as the starting material and with use of the Wittig and modified Julia olefination reactions as key steps.

d-glucose - Raney nickel - Wittig reaction - modified Julia olefination

References

1a Gustafson K. Roman M. Fenical W. J. Am. Chem. Soc.  1989,  111:  7519 

1b Rychnovsky SD. Skalitzky DJ. Pathirana C. Jensen PR. Fenical W. J. Am. Chem. Soc.  1992,  114:  671 

2a Kim H.-H. Kim W.-G. Ryoo I.-J. Kim C.-J. Suk J.-E. Han K.-H. Hwang S.-Y. Yoo I.-D. J. Microbiol. Biotechnol.  1997,  7:  429 

2b Jaruchoktaweechai C. Suwanborirus K. Tanasupawatt S. Kittakoop P. Menasveta P. J. Nat. Prod.  2000,  63:  984 

2c Nagao T. Adachi K. Sakai M. Nishijima M. Sano H. J. Antibiot.  2001,  54:  333 

3a Smith AB. Ott GR. J. Am. Chem. Soc.  1996,  118:  13095 

3b Kim Y. Singer RA. Carreira EM. Angew. Chem. Int. Ed.  1998,  37:  1261 

3c Marino JP. McClure MS. Holub DP. Comasseto JV. Tucci FC. J. Am. Chem. Soc.  2002,  124:  1664 

For partial syntheses, see:

4a Benvegnu T. Schio L. Le Floch Y. Gree R. Synlett  1994,  505 

4b Donaldson WA. Bell PT. Wang Z. Bennett DW. Tetrahedron Lett.  1994,  35:  5829 

4c Boyce RJ. Pattenden G. Tetrahedron Lett.  1996,  37:  3501 

4d Benvegnu T. Toupet L. Gree R. Tetrahedron  1996,  52:  11811 

4e Prahlad V. Donaldson WA. Tetrahedron Lett.  1996,  37:  9169 

4f Gonzalez A. Aiguade J. Urp F. Villarasa J. Tetrahedron Lett.  1996,  37:  8949 

4g Tanimori S. Morita Y. Tsubota M. Nakayama M. Synth. Commun.  1996,  26:  559 

4h Bärmann H. Prahlad V. Tao C. Yun YK. Wang Z. Donaldson WA. Tetrahedron  2000,  56:  2283 

4i Li S. Xu R. Bai D. Tetrahedron Lett.  2000,  41:  3463 

4j Hoffmann HMR. Vakalopoulos A. Org. Lett.  2001,  3:  177 

4k Li S. Donaldson WA. Synthesis  2003,  2064 

4l Fukuda A. Kobayashi Y. Kimachi T. Takemoto Y. Tetrahedron  2003,  59:  9305 

4m Bonini C. Chiummiento L. Pullez M. Solladié G. Colobert F. J. Org. Chem.  2004,  69:  5015 

4n Li S. Xiao X. Yan X. Liu X. Xu R. Bai D. Tetrahedron  2005,  61:  11291 

For a total synthesis of an analogue of macrolactin-A, see:

4o Kobayashi Y. Fukuda A. Kimachi T. Ju-ichi M. Takemoto Y. Tetrahedron Lett.  2004,  45:  677 

4p Kobayashi Y. Fukuda A. Kimachi T. Ju-ichi M. Takemoto Y. Tetrahedron  2005,  61:  2607 

5a Yadav JS. Prathap I. Tadi BP. Tetrahedron Lett.  2006,  47:  3773 

5b Yadav JS. Rao KV. Reddy MS. Prasad AR. Tetrahedron Lett.  2006,  47:  4393 

5c Yadav JS. Reddy MS. Prasad AR. Tetrahedron Lett.  2005,  46:  2133 

6 Schaus SE. Brandes BD. Larrow JF. Tokunaga M. Hansen KB. Gould AE. Furrow ME. Jacobsen EN. J. Am. Chem. Soc.  2002,  124:  1307 

7 Prakash KR. Rao SP. Tetrahedron  1993,  49:  1505 

8a Blakemore PR. J. Chem. Soc., Perkin Trans. 1  2002,  2563 ; and references cited therein

8b Harris JM. O’Doherty GA. Tetrahedron  2001,  57:  5161 

8c Blakemore PR. Cole WJ. Kocienski PJ. Morley A. Synlett  1998,  26 

9 Yamagushi M. Hirao I. Tetrahedron Lett.  1983,  24:  391 

10

Propylene oxide 8a was obtained by a literature procedure [6] and is easily isolated from the more polar diol 8b by distillation (Scheme [4] ). Compound 8a: [α]_D ²⁵ +11.5 (neat) [Lit. [6] for S-isomer of 8a: [α]_D ²⁵ -11.7 (neat)].

11 Mitsunobu O. Synthesis  1981,  1 ; and references cited therein