Efficient Synthesis of the C1-C13 Fragment of Bistramide A

Abstract

Herein we report an efficient synthesis of the C1-C13 fragment of bistramide A from (S)-1,2,4-butanetriol and Roche ester in 14 steps and 13% overall yield.

Key words

bistramide - tetrahydropyran - oxa-Michael - Julia-modified olefination

References and Notes

• 1 Gouiffès D. Moreau S. Helbecque N. Bernier JL. Hénichart JP. Barbin Y. Laurent D. Verbist JF. Tetrahedron  1988,  44:  451 
• 2 Biard JF. Roussakis C. Kornprobst JM. Gouiffes-Barbin D. Verbist JF. Cotelle P. Foster MP. Ireland CM. Debitus C. J. Nat. Prod.  1994,  7:  1336 
• 3 Pusset J. Maillere B. Debitus C. J. Nat. Toxins  1996,  5:  1 
• 4 Griffiths G. Garrone B. Deacon E. Owen P. Pongracz J. Mead G. Bradwell A. Watters D. Lord J. Biochem. Biophys. Res. Commun.  1996,  222:  802 
• 5 Statsuk AV. Bai R. Baryza JL. Verma VA. Hamel E. Wender PA. Kozmin SA. Nat. Chem. Biol.  2005,  1:  383 
• 6a Statsuk AV. Liu D. Kozmin SA. J. Am. Chem. Soc.  2004,  126:  9546 
• 6b Crimmins MT. DeBaillie AC. J. Am. Chem. Soc.  2006,  128:  4936 
• 6c Lowe JT. Wrona IE. Panek JS. Org. Lett.  2007,  9:  327 
• 6d Yadav JS. Chetia L. Org. Lett.  2007,  9:  4587 
• 6e Wipf P. Uto Y. Yoshimura S. Chem. Eur. J.  2002,  8:  1670 
• 7 Bates RW. Palani K. Tetrahedron Lett.  2008,  49:  2832 
• 8 Hiebel MA. Pelotier B. Piva O. Tetrahedron Lett.  2010,  51:  5091 
• 10 Erickson KL. Gustafson KR. Pannell LK. Beutler JA. Boyd M. J. Nat. Prod.  2002,  65:  1303 
• 11 Pereira AR. McCue CF. Gerwick WH. J. Nat. Prod.  2010,  73:  217 
• 12 Strand D. Norrby P. Rein T. J. Org. Chem.  2006,  71:  1879 
• 14 Gallagher PO. McErlean CSP. Jacobs MF. Watters DJ. Kitching W. Tetrahedron Lett.  2002,  43:  531 

9

^¹H NMR (300 MHz, CDCl₃): δ = 0.82 (d, J = 6.9 Hz, 3 H), 1.32 (m, 2 H), 1.62 (m, 4 H), 2.00 (m, 1 H), 2.20 (dd, J = 2.9, 14.5 Hz, 1 H), 2.87 (dd, J = 12.7, 14.5 Hz, 1 H), 3.78 (m, 1 H), 3.96 (m, 1 H), 4.33 (m, 1 H) ppm. ESI-MS: m/z = 391.2 [M + Na]⁺. CCDC 843221 contains the supplementary crystallographic data for this structure. These data can be obtained free of charge from The Cambridge Crystallog-raphic Data Centre via http://www.ccdc.ac.uk/data_request/cif.

13

^¹H NMR (400 MHz, CDCl₃): δ = 0.82 (d, J = 7.0 Hz, 3 H), 1.28 (t, J = 7.2 Hz, 3 H), 1.32-1.39 (m, 1 H), 1.53-1.69 (m, 6 H), 1.93-2.06 (m, 1 H), 2.33 (dd, J = 4.1, 13.5 Hz, 1 H), 2.80 (dd, J = 11.8, 13.5 Hz, 1 H), 2.94-3.01 (m, 1 H), 3.55-3.66 (m, 1 H), 3.68-3.75 (m, 1 H), 3.81-3.91 (m, 1 H), 4.16 (q, J = 7.1 Hz, 2 H), 4.28 (dt, J = 4.9, 4.9, 11.8 Hz, 1 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 172.9 (C), 74.7 (CH), 68.0 (CH), 61.1 (CH₂), 60.2 (CH₂), 38.3 (CH₂), 33.1 (CH), 32.6 (CH₂), 31.8 (CH₂), 26.8 (CH₂), 17.4 (CH₃), 14.2 (CH₃). ESI-MS: m/z = 253 [M + Na]⁺. ESI-HRMS: m/z calcd for C₁₂H₂₂O₄Na [M + Na]⁺: 253.1410; found: 253.1412.