Synthesis and Application of an Enantiomerically Pure Triflate Analogue of Microbially Derived 3-Halo-cis-1,2-dihydrocatechol Acetonides

Fenglai Sun; Peter Metz

doi:10.1055/s-0032-1318214

Synlett, Table of Contents

Synlett 2013; 24(4): 457-460
DOI: 10.1055/s-0032-1318214

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Synthesis and Application of an Enantiomerically Pure Triflate Analogue of Microbially Derived 3-Halo-cis-1,2-dihydrocatechol Acetonides

Fenglai Sun

Fachrichtung Chemie und Lebensmittelchemie, Organische Chemie I, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany Fax: +49(351)46333162 Email: peter.metz@chemie.tu-dresden.de

,

Peter Metz*

Fachrichtung Chemie und Lebensmittelchemie, Organische Chemie I, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany Fax: +49(351)46333162 Email: peter.metz@chemie.tu-dresden.de

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Abstract

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Dedicated to Professor Lutz F. Tietze on the occasion of his 70th birthday.

Abstract

(1S,2S)-3-Trifloxy-cis-1,2-dihydrocatechol acetonide, a useful chiral building block, was prepared from d-ribose in good overall yield using a carbonyl allylation and a ring-closing metathesis as the key C–C bond-forming steps. Negishi cross-coupling of this triflate with a serine-derived organozinc iodide proceeded efficiently to afford an α-amino acid derivative as a potential precursor for scabrosin esters (ambewelamides).

Key words

chiral pool - allylation - metathesis - cross-coupling - scabrosin esters

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References

References and Notes
1 Review: Hudlicky T, Reed JW. Synlett 2009; 685
2 Boyd DR, Sharma ND, Llamas NM, Malone JF, O’Dowd CR, Allen CC. R. Org. Biomol. Chem. 2005; 3: 1953 ; and literature cited therein
3 Boyd DR, Blacker J, Byrne B, Dalton H, Hand MV, Kelly SC, More O’Ferrall RA, Rao SN, Sharma ND, Sheldrake GN. J. Chem. Soc., Chem. Commun. 1994; 313

4a Austin KA. B, Elsworth JD, Banwell MG, Willis AC. Org. Biomol. Chem. 2010; 8: 751
4b Heguaburu V, Mandolesi Sá M, Schapiro V, Pandolfi E. Tetrahedron Lett. 2008; 49: 6787
4c Austin KA. B, Banwell MG, Willis AC. Org. Lett. 2008; 10: 4465
4d Boyd DR, Sharma ND, Byrne B, Hand MV, Malone JF, Sheldrake GN, Blacker J, Dalton H. J. Chem. Soc., Perkin Trans. 1 1998; 1935
4e Boyd DR, Hand MV, Sharma ND, Chima J, Dalton H, Sheldrake GN. J. Chem. Soc., Chem. Commun. 1991; 1630

5 Hanazawa T, Okamoto S, Sato F. Tetrahedron Lett. 2001; 42: 5455

6a Ernst-Russell MA, Chai CL. L, Hurne AM, Waring P, Hockless DC. R, Elix JA. Aust. J. Chem. 1999; 52: 279
6b Williams DE, Bombuwala K, Lobkovsky E, de Silva ED, Karunaratne V, Allen TM, Clardy J, Andersen RJ. Tetrahedron Lett. 1998; 39: 9579
6c Moerman KL, Chai CL. L, Waring P. Toxicol. Appl. Pharmacol. 2003; 190: 232
6d Chai CL. L, Elix JA, Huleatt PB, Waring P. Bioorg. Med. Chem. 2004; 12: 5991
6e Middleton MD, Peppers BP, Diver ST. Tetrahedron 2006; 62: 10528

7a Codelli JA, Puchlopek AL. A, Reisman SE. J. Am. Chem. Soc. 2012; 134: 1930
7b Nicolaou KC, Totokotsopoulos S, Giguère D, Sun Y.-P, Sarlah D. J. Am. Chem. Soc. 2011; 133: 8150
7c Gross U, Nieger M, Bräse S. Chem. Eur. J. 2010; 16: 11624

8 Moon HR, Choi WJ, Kim HO, Jeong LS. Tetrahedron: Asymmetry 2002; 13: 1189
9 Yadav JS, Satheesh G, Murthy CV. S. R. Org. Lett. 2010; 12: 2544
10 Rolandsgard M, Baldawi S, Sirbu D, Bjørnstad V, Rømming C, Undheim K. Tetrahedron 2005; 61: 4129
11 Oppolzer W, Spivey AC, Bochet CG. J. Am. Chem. Soc. 1994; 116: 3139
12 Jin YH, Liu P, Wang J, Baker R, Huggins J, Chu CK. J. Org. Chem. 2003; 68: 9012
13 Ross AJ, Lang HL, Jackson RF. W. J. Org. Chem. 2010; 75: 245
14 Compound 1 (R = I) was purchased from Questor, Queen’s University of Belfast, Northern Ireland, in March 2010 (10 g = £ 850).