Synthesis 2016; 48(11): 1700-1710
DOI: 10.1055/s-0035-1561607
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Iterative Hydration of Polyene Strategy to Cryptocaryols A and B

Thomas J. Hunter
b   MilliporeSigma, 645 Science Drive, Madison, WI 53711, USA
,
Yanping Wang
a   Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA   Email: G.ODoherty@neu.edu
,
Jiamin Zheng
a   Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA   Email: G.ODoherty@neu.edu
,
George A. O’Doherty*
a   Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA   Email: G.ODoherty@neu.edu
› Author Affiliations
Further Information

Publication History

Received: 21 February 2016

Accepted after revision: 11 March 2016

Publication Date:
13 April 2016 (online)


Abstract

The development of two iterative asymmetric hydration approaches to the synthesis of all syn- and syn/anti/syn-1,3,5,7-tetraol motifs is described. These pseudo-symmetric products are synthetic precursors for 1,3-hexol products. The utility of the route to the all syn-1,3,5,7-tetraol diastereoisomer was demonstrated with its use in the synthesis of cryptocaryols A and B, as well as, stereoisomers.

Supporting Information

 
  • References

  • 1 Grkovic T, Blees JS, Colburn NH, Schmid T, Thomas CL, Henrich CJ, McMahon JB, Gustafson KR. J. Nat. Prod. 2011; 74: 1015
    • 2a Kobayashi Y, Tan C.-H, Kishi Y. Helv. Chim. Acta 2000; 83: 2562
    • 2b Higashibayashi S, Czechtizky W, Kobayashi Y, Kishi Y. J. Am. Chem. Soc. 2003; 125: 14379
  • 3 Snatzke G. Angew. Chem., Int. Ed. Engl. 1968; 7: 14
  • 4 Wang Y, O’Doherty GA. J. Am. Chem. Soc. 2013; 135: 9334
    • 5a Dias LC, Kuroishi PK, de Lucca EC. Org. Biomol. Chem. 2015; 13: 3575
    • 5b Brun E, Bellosta V, Cossy J. J. Org. Chem. 2015; 80: 8668
    • 5c Bredenkamp A, Wegener M, Hummel S, Haring AP, Kirsch SF. Chem. Commun. 2016; 52: 1875
  • 6 Mohapatra reported the synthesis of purported cryptocaryol A (3) and mistakenly reported it as cryptocaryol A (1), see: Reddy DS, Mohapatra DK. Eur. J. Org. Chem. 2013; 1051
  • 7 Cuccarese MF, Wang Y, Beuning PJ, O’Doherty GA. ACS Med. Chem. Lett. 2014; 5: 522

    • For other approaches to 1,3-syn-polyols, see:
    • 8a Rychnovsky SD. Chem. Rev. 1995; 95: 2021
    • 8b Rychnovsky SD, Hoye RC. J. Am. Chem. Soc. 1994; 116: 1753
    • 8c Rychnovsky SD, Khire UR, Yang G. J. Am. Chem. Soc. 1997; 119: 2058
    • 8d Carreira EM, Singer RA, Lee W. J. Am. Chem. Soc. 1994; 116: 8837
    • 8e Evans DA, Murry JA, Kozlowski MC. J. Am. Chem. Soc. 1996; 118: 5814
    • 8f Evans DA, Coleman PJ, Cote B. J. Org. Chem. 1997; 62: 788
    • 8g Paterson I, Oballa RM, Norcross RD. Tetrahedron Lett. 1996; 37: 8581
    • 8h Paterson I, Gibson KR, Oballa RM. Tetrahedron Lett. 1996; 37: 8585

      For iterative asymmetric hydration of polyenes, see:
    • 9a Wang Y, Xing Y, Zhang Q, O’Doherty GA. Chem. Commun. 2011; 47: 8493
    • 9b Ahmed MdM, Mortensen MS, O’Doherty GA. J. Org. Chem. 2006; 71: 7741
    • 9c Hunter TJ, O’Doherty GA. Org. Lett. 2001; 3: 1049

      For the syntheses of related 1,3-polyol natural products, see:
    • 10a Hunter TJ, O’Doherty GA. Org. Lett. 2001; 3: 2777
    • 10b Smith CM, O’Doherty GA. Org. Lett. 2003; 5: 1959
    • 10c Garaas SD, Hunter TJ, O’Doherty GA. J. Org. Chem. 2002; 67: 2682

    • For alternative approaches, see ref. 5 and:
    • 10d Melillo B, Smith AB. Org. Lett. 2013; 15: 2282
    • 11a Guo H, Mortensen MS, O’Doherty GA. Org. Lett. 2008; 10: 3149
    • 11b Gao D, O’Doherty GA. Org. Lett. 2010; 12: 3752
    • 11c Li M, O’Doherty GA. Org. Lett. 2006; 8: 6087
    • 11d Li M, O’Doherty GA. Org. Lett. 2006; 8: 3987
  • 12 Evans DA, Gauchet-Prunet JA. J. Org. Chem. 1993; 58: 2446
    • 13a Xu D, Crispino GA, Sharpless KB. J. Am. Chem. Soc. 1992; 114: 7570
    • 13b Zhang Y, O’Doherty GA. Tetrahedron 2005; 61: 6337
    • 13c Becker H, Soler MA, Sharpless KB. Tetrahedron 1995; 51: 1345
    • 13d Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994; 94: 2483
    • 14a All levels of enantioinduction were determined by HPLC analysis (8% i-PrOH/hexane, Chiralcel OD) and/or Mosher ester analysis.
    • 14b Sullivan GR, Dale JA, Mosher HS. J. Org. Chem. 1973; 38: 2143
    • 14c Yamaguchi S, Yasuhara F, Kabuto KT. Tetrahedron 1976; 32: 1363
    • 15a Tsuji J, Minami I. Acc. Chem. Res. 1987; 20: 140
    • 15b Hughes G, Lautens M, Wen C. Org. Lett. 2000; 2: 107

      For alternative approaches to δ-hydroxy-1-enoates see:
    • 16a Fleming I. Bull. Soc. Chem. Fr. 1981; 2: 7
    • 16b Barloy-Da Silva C, Benkouider A, Pale P. Tetrahedron Lett. 2000; 41: 3077
    • 16c Albaugh-Robertson P, Katzenellenbogen JA. J. Org. Chem. 1983; 48: 5288
    • 16d Miyazawa M, Matsuoka E, Sasaki S, Oonuma S, Maruyam K, Miyashita M. Chem. Lett. 1998; 109
    • 16e Keck GE, Palani A, McHardy SF. J. Org. Chem. 1994; 59: 3113
    • 16f Solladie G, Gressot L, Colobert F. Eur. J. Org. Chem. 2000; 357
    • 17a Burden RS, Crombie L. J. Chem. Soc. C 1969; 2477
    • 17b Bohlmann F, Zdero C. Chem. Ber. 1973; 106: 3779
    • 17c Roush WR. J. Am. Chem. Soc. 1980; 102: 1390
    • 17d Evans DA, Fitch DM. J. Org. Chem. 1997; 62: 454
    • 17e Posner GH, Lee JK, White MC, Hutchings RH, Dai H, Kachinski JL, Dolan P, Kensler TW. J. Org. Chem. 1997; 62: 3299
    • 17f Barrett AG. M, Hamprecht D, White AJ. P, Williams DJ. J. Am. Chem. Soc. 1997; 119: 8608
    • 17g Takacs JM, Jaber MR, Clement F, Walters C. J. Org. Chem. 1998; 63: 6757
    • 17h Nazare M, Waldmann H. Chem. Eur. J. 2001; 7: 3363
    • 17i Sun M, Deng Y, Batyreva E, Sha W, Salomon RG. J. Org. Chem. 2002; 67: 3575
    • 17j Tsuzuki T, Tanaka K, Kuwahara S, Miyazawa T. Lipids 2005; 40: 147
    • 17k Barth R, Mulzer J. Angew. Chem. Int. Ed. 2007; 46: 5791
    • 17l Markiewicz JT, Schauer DJ, Lofstedt J, Corden SJ, Wiest O, Helquist P. J. Org. Chem. 2010; 75: 2061
    • 18a Kubota K, Leighton JL. Angew. Chem. Int. Ed. 2003; 115: 976
    • 18b Chalifoux WA, Reznik SK, Leighton JL. Nature 2012; 487: 86
  • 19 Scholl M, Trnka TM, Morgan JP, Grubbs RH. Tetrahedron Lett. 1999; 40: 2247
  • 20 Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R. J. Am. Chem. Soc. 1995; 117: 7562
    • 21a Grubbs RH. Angew. Chem. Int. Ed. 2006; 45: 3760
    • 21b Gosh AK, Bilcer G. Tetrahedron Lett. 2000; 41: 1003
    • 21c Boger DL, Ichikawa D, Zhong W. J. Am. Chem. Soc. 2001; 123: 4161
    • 21d Reddy MV. R, Rearick JP, Hoch N, Ramachandran PV. Org. Lett. 2001; 3: 19
    • 21e Smith AB, Brandt BM. Org. Lett. 2001; 3: 1685
    • 21f Reddy MV. R, Yucel AJ, Ramachandran PV. J. Org. Chem. 2001; 66: 2512
    • 21g Garaas SD, Hunter TJ, O’Doherty GA. J. Org. Chem. 2002; 67: 2682