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.

Key words

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

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)].