Concise Stereoselective Total Synthesis of (+)-Mueggelone

REFERENCES

• Olaf , P. ; Gabriele , M. K. ; Anthony , D. W. ; Ingrid , C. ; Axel , O. Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos aquae . J. Nat. Prod. 1997 , 60 , 1298 – 1300 .
   PubMed Web of Science ®Google Scholar
• (a) Ishigami , K. ; Motoyoshi , H. ; Kithara , T. First total synthesis and determination of the absolute configuration of mueggelone . Tetrahedron 2001 , 57 , 3899 – 3908 ; (b) Yadav , J. S. ; Somaiah , R. ; Ravindar , K. ; Chandraiah , L. Stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development . Tetrahedron Lett. 2008 , 49 , 2848 – 2850 ; (c) Ishigami , K. ; Motoyoshi , H. ; Kithara , T. First total synthesis of mueggelone . Tetrahedron Lett. 2000 , 41 , 8897 – 8901 .
   Google Scholar
• Toshio , H. ; Mai , O. ; Hirotake , M. Enantiocontrolled synthesis of naturally occurring octadecadienoic acid derivatives, self-defensive substances against rice blast disease, by means of the Sharpless asymmetric epoxidation of unsymmetrical divinylmethanol . J. Chem. Soc., Perkin Trans. 1 1999 , 23 – 30 .
   Google Scholar
• (a) Sharpless , K. B. ; Katsuki , T. The first practical method for asymmetric epoxidation . J. Am. Chem. Soc. 1980 , 102 , 5974 – 5976 ; (b) Gao , Y. ; Hanson , R. M. ; Klunder , J. M. ; Ko , S. Y. ; Masamune , H. ; Sharpless , K. B. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization . J. Am Chem. Soc. 1987 , 109 , 5765 – 5780 .
   Web of Science ®Google Scholar
• Corey , E. J. ; Martaf , A. ; Laguzza , B. C. Total synthesis of 5s,12s-dihydroxy-6,10-E,8,14-Z-eicosatetraenoic acid (5S,12S-di-hete) (2), a new human metabolite of arachidonic acid . Tetrahedron Lett. 1981 , 22 , 3339 – 3342 .
   Web of Science ®Google Scholar
• Schaus , S. E. ; Brandes , B. D. ; Larrow , J. F. ; Tokunaga , M. ; Hansen , K. B. ; Gould , A. E. ; Furrow , M. E. ; Jacobsen , E. N. Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes: Practical synthesis of enantioenriched terminal epoxides and 1,2-diols . J. Am. Chem. Soc. 2002 , 124 , 1307 – 1315 .
   PubMed Web of Science ®Google Scholar
• Alcaraz , L. ; Harnett , J. J. ; Mioskowski , C. ; Martel , J. P. ; Le Gall , T. ; Shin , D. S. ; Falck , J. R. Novel conversion of epoxides to one carbon homologated allylic alcohols by dimethylsulfonium methylide . Tetrahedron Lett. 1994 , 35 , 5449 – 5452 .
   Web of Science ®Google Scholar
• Prakash , C. ; Saleh , S. ; Blair , I. A. Selective de-protection of silyl ethers . Tetrahedron Lett. 1989 , 30 , 19 – 22 .
   Web of Science ®Google Scholar
• (a) Van den Bos , L. J. ; Litjens , R. E. J. N. ; Van den Berg , R. J. B. H. N. ; Verkleeft , H. S. ; Vander Marel , G. A. Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis. Org. Lett. 2005, 7, 2007–2010; (b) Yadav , J. S. ; Reddy , Ch. S. Highly enantioselective construction of axial chirality by palladium-catalyzed cycloisomerization of N-alkenyl arylethynylamides. Org. Lett. 2009, 11, 1805–1808.
   PubMed Web of Science ®Google Scholar
• (a) Shiina , I. ; Kikuchi , T. ; Sasaki , A. The first total synthesis of (−) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization . Org. Lett. 2006 , 8 , 4955 – 4958 ; (b) Shiina , I. ; Ibuka , R. ; Kubota , M. A new condensation reaction for the synthesis of carboxylic esters from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride . Chem. Lett. 2002 , 286 – 287 ; (c) Shiina , I. ; Kubota , M. ; Oshiumi , H. ; Hashizume , M. An effective use of benzoic anhydride and its derivatives for the synthesis of carboxylic esters and lactones: a powerful and convenient mixed anhydride method promoted by basic catalysts . J. Org. Chem. 2004 , 69 , 1822 – 1830 .
   PubMed Web of Science ®Google Scholar
• McDonald , F. E. ; Wei , X. Concise, regioselective synthesis of the abc tristetrahydropyran of thyrsiferol and venustatriol . Org. Lett. 2002 , 4 , 593 – 595 .
   PubMedGoogle Scholar