Synthesis of Gymnoascolide A

Abstract

Recently isolated 4-benzyl-3-phenylfuran-2,5-dione and antifungal gymnoascolide A have been synthesized using the chemoselective S_N2′ coupling of phenylmagnesium bromide with dimethyl 2-(bromomethyl)fumarate, chemoselective allylic substitution of bromide in 3-(bromomethyl)-4-phenylfuran-2,5-dione with phenylmagnesium bromide and regioselective N-Selectride-induced reduction of 3-benzyl-4-phenylfuran-2,5-dione as the key reactions.

Key words

dimethyl (bromomethyl)fumarate - S_N2′ Grignard coupling reaction - functionalized maleic anhydrides - regioselective reduction - gymnoascolide A

References

• 1 Clark B. Capon RJ. Lacey E. Tennant S. Gill JH. Bulheller B. Bringmann G. J. Nat. Prod.  2005,  68:  1226 
• 2 Hosoe T. Iizuka T. Komai S.-I. Wakana D. Itabashi T. Nozawa K. Fukushima K. Kawai K.-I. Phytochemistry  2005,  66:  2776 
• 3 Hamasaki T. Nakajima H. Yokota T. Kimura Y. Agric. Biol. Chem.  1983,  47:  891 
• 4 Lin Y. Li H. Jiang G. Zhou S. Vrijmoed LLP. Jones EBG. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  2002,  41:  1542 
• 5 Fujimoto H. Satoh Y. Yamaguchi K. Yamazaki M. Chem. Pharm. Bull.  1998,  46:  1506 
• 6 Momose T. Tanabe G. Tsujimori H. Muraoka O. Chem. Pharm. Bull.  1992,  40:  2525 
• 7a Patel RM. Argade NP. J. Org. Chem.  2007,  72:  4900 
• 7b Baag MM. Puranik VG. Argade NP. J. Org. Chem.  2007,  72:  1009 
• 7c Haval KP. Argade NP. Synthesis  2007,  2198 
• 7d Kar A. Argade NP. J. Org. Chem.  2002,  67:  7131 
• 7e Argade NP. Balasubramaniyan V. Heterocycles  2000,  53:  475  and references 7a-e cited therein
• 8 Schreiber J. Ann. Chim.  1947,  2:  84