Diastereoselective Synthesis of syn-Alkanetriols from a Glyceral Derivative via k-Selectride Reduction: Application to the Synthesis of a Pheromone of the Sugarcane Weevils

Abstract

k-selectride reduction of commercially available d-mannitol­ derived ketones 2b-i produced the corresponding alcohols 3b-i in good yields and with absolute syn-selectivity in almost all the cases. It was proposed that the bulky cyclohexylidene moiety of 3 has a significant role in favoring the reduction with k-selectride via Felkin-Anh model. Subsequently, one of the reduction product 3c has been exploited to synthesize the pheromone I of sugarcane weevil.

Key words

k-selectride - reduction - syn-alkanetriols - selectivity - Felkin-Anh model

References

• 1 Jarowicki K. Kocienski P. J. Chem. Soc., Perkin Trans. 1  2001,  2109 ; and references cited therein
• 2a Chattopadhyay A. Mamdapur VR. J. Org. Chem.  1995,  60:  585 
• 2b Chattopadhyay A. J. Org. Chem.  1996,  61:  6104 
• 2c Chattopadhyay A. Hassarajani SA. Dhotare B. J. Org. Chem.  1999,  64:  6874 
• 2d Chattopadhyay A. Tetrahedron: Asymmetry  1997,  8:  2727 
• 2e Chattopadhyay A. Salaskar A. J. Chem. Soc., Perkin Trans.1  2002,  785 
• 2f Dhotare B. Hassarajani SA. Chattopadhyay A. Enantiomer  1999,  4:  431 
• 3a Micolajczyk M. Mikina M. Jankoyaak A. J. Org. Chem.  2000,  65:  5130 
• 3b Compostella F. Franchini L. Giovenzana GB. Tetrahedron: Asymmetry  2002,  13:  867 
• 3c Merino P. Castilo E. Franco S. J. Org. Chem.  1998,  63:  2371 
• 3d Sharma A. Chattopadhyay S. Tetrahedron: Asymmetry  1999,  10:  883 
• 4 Puigjaner C. Vidal-Ferran A. Moyano A. Pericas MA. Reira A. J. Org. Chem.  1999,  64:  7902 
• 5a Midland MM. Tramontano A. Kazubski A. Graham RS. Tsai DJS. Cardin DB. Tetrahedron  1984,  40:  1371 
• 5b Midland MM. Graham RS. Org. Synth.  1985,  63:  57 
• 5c Chun J. Byun H. Bittman R. J. Org. Chem.  2003,  68:  348 
• 6 Desroy N. Roux RL. Phansavath P. Chiummeiento L. Bonini C. Genet JP. Tetrahedron Lett.  2003,  44:  1763 
• 7a Nakamura K. Kitayama T. Inoue Y. Ohno A. Tetrahedron  1990,  46:  7471 
• 7b Nakamura K. Kawai Y. Oka A. Ohno A. Tetrahedron Lett.  1989,  30:  2245 
• 7c Drauz K. Waldmann H. Enzyme Catalysis in Organic Synthesis   Vol. II:  VCH; Weinheim: 1995.  p.595 
• 8 Oishi T. Nakata T. Acc. Chem. Res.  1984,  17:  338 
• 9a Akiyama T. Nishimoto H. Kuwata T. Ozaki S. Bull. Chem. Soc. Jpn.  1994,  67:  180 
• 9b Dehoux C. Mothien C. Baltas M. Gorricon L. Synthesis  2000,  1409 
• 9c Dondoni A. Synthesis  1998,  1681 ; and references cited therein
• 10 Trost BM. Yeh VSC. Org. Lett.  2002,  4:  3513 ; and references cited therein
• 11 Nadkarni D. Hallissey J. Mijica C. J. Org. Chem.  2003,  68:  594 
• 12 Dhotare B. Chattopadhyay A. Synthesis  2001,  1337 
• 13 Corey EJ. Suggs T. Tetrahedron Lett.  1973,  2764 
• 14a Cherest M. Felkin H. Tetrahedron Lett.  1968,  2205 
• 14b Anh NT. Top. Curr. Chem.  1980,  88:  145 
• 15 Mengel A. Reiser O. Chem. Rev.  1999,  99:  1191 
• 16a Marshall JA. Piettre A. Paige MA. Valeriote F. J. Org. Chem.  2003,  68:  1771 
• 16b Avedissian H. Sinha SC. Yazbak A. Sinha A. Neogi P. Sinha SC. Keinan E. J. Org. Chem.  2000,  65:  6035 
• 17 Grauert M. Schöllkopf U. Liebigs Ann. Chem.  1985,  1817 
• 18a Kolb HC. VanNieuwenhze S. Sharpless KB. Chem. Rev.  1994,  94:  2483 ; and references cited therein
• 18b Sharpless KB. Amberg W. Benanni YL. Crispino GA. Hartung J. Jeong K. Kwyong H. Morikawa K. Wang J. Xu D. Zhang X. J. Org. Chem.  1992,  57:  2768 
• 19a Roush WR. Waltz AE. Hong LK. J. Am. Chem. Soc.  1985,  107:  8186 
• 19b Sato F. Kobayashi O. Chiba T. Takeda Y. Kasakabe M. J. Chem. Soc., Chem. Commun.  1985,  1636 
• 20 Baraldi P. Zarbin PHG. Vieira PC. Correa AG. Tetrahedron: Asymmetry  2002,  13:  621 ; and references cited therein