Diels–Alder Reactions of γ-Hydroxybutenolides: Approach to the Himbacine Tricyclic Core

William H. Miles; Dasan M. Thamattoor; Ryan E. Cerbone; Daniel J. Beideman; Samantha M. Zeiders; Natalie E. Jasiewicz; Stephanie M. Petersen; Barbara J. Naimoli; Joseph V. Leo; Ida B. G. Suarsana; Jason S. George; Nicholas J. Albano

doi:10.1055/s-0035-1561348

Synthesis, Table of Contents

Synthesis 2016; 48(06): 924-934
DOI: 10.1055/s-0035-1561348

paper

Diels–Alder Reactions of γ-Hydroxybutenolides: Approach to the Himbacine Tricyclic Core

William H. Miles*

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Dasan M. Thamattoor

^bDepartment of Chemistry, Colby College, Waterville, ME 04901, USA

,

Ryan E. Cerbone

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Daniel J. Beideman

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Samantha M. Zeiders

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Natalie E. Jasiewicz

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Stephanie M. Petersen

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Barbara J. Naimoli

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Joseph V. Leo

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Ida B. G. Suarsana

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Jason S. George

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

,

Nicholas J. Albano

^aDepartment of Chemistry, Lafayette College, Easton, PA 18042, USA Email: milesw@lafayette.edu

› Author Affiliations

Abstract

All articles of this category

Abstract

The Diels–Alder reaction of γ-hydroxybutenolides with dienes gave good yields of cycloadducts under thermal and Lewis acid catalyzed conditions. The application of this methodology to a more complex system was demonstrated by the synthesis of a model system for the tricyclic himbacine core. The stereo- and regioselective Diels–Alder reaction established three of the stereogenic centers, with the fourth stereogenic center secured by diastereoselective alkylation of the cycloadduct.

Key words

γ-hydroxybutenolide - Diels–Alder reaction - himbacine - Lewis acid catalysis - isomerization

Full Text

References

References
1 Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668

2a Miles WH, Cohen EM, Naimoli BJ. Synth. Commun. 2013; 43: 1980 ; and references cited therein
2b Mukherjee S, Corey EJ. Org. Lett. 2010; 12: 1024
2c Kakushima M, Scott DG. Can. J. Chem. 1979; 57: 1399
2d Danishefsky S, Prisbylla MP, Hiner S. J. Am. Chem. Soc. 1978; 100: 2918

3a Kowalski CJ, Lal GS. J. Am. Chem. Soc. 1988; 110: 3693
3b Zhang YD, Tang YF, Luo TP, Shen J, Chen JH, Yang Z. Org. Lett. 2006; 8: 107
3c Hu QY, Zhou G, Corey EJ. J. Am. Chem. Soc. 2004; 126: 13708

4 Feringa BL, De Lange B, Jansen JF. G. A, De Jong JC, Lubben M, Faber W, Schudde EP. Pure Appl. Chem. 1992; 64: 1865
5 Simple γ-alkyl-γ-hydroxybutenolides are at slow exchange in the ¹H NMR at ambient temperature, with the presence of the chain tautomer as high as 5%
6 For a review of the synthetic applications of γ-hydroxybutenolides, see: Miles WH. Curr. Org. Synth. 2014; 11: 244

7a Miller KK, Zhang P, Nishizawa-Brennen Y, Frost JW. ACS Sustain. Chem. Eng. 2014; 2: 2053
7b Furuta K, Miwa Y, Iwanaga K, Yamamoto H. J. Am. Chem. Soc. 1988; 110: 6254
7c Al-Zoubi RM, Marion O, Hall DG. Angew. Chem. Int. Ed. 2008; 47: 2876
7d Zheng HC, Hall DG. Tetrahedron Lett. 2010; 51: 3561
7e Ryu DH, Corey EJ. J. Am. Chem. Soc. 2003; 125: 6388

8a Magnus P, Cairns PM. J. Am. Chem. Soc. 1986; 108: 217
8b Magnus P, Cairns PM, Moursounidis J. J. Am. Chem. Soc. 1987; 109: 2469

9a Noutsias D, Vassilikogiannakis G. Org. Lett. 2012; 14: 3565
9b Tu NP. W, Yip JC, Dibble PW. Synthesis 1996; 77
9c Sánchez-Obregón R, Salmón M, Walls F. Bol. Inst. Quim. Univ. Nacl. Autón. Méx. 1970; 22: 16 ; Chem. Abstr. 1971, 74, 140602

10a Lee GC. M, Syage ET, Harcourt DA, Holmes JM, Garst ME. J. Org. Chem. 1991; 56: 7007
10b Adam W, Rodriguez A. Tetrahedron Lett. 1981; 22: 3505
10c Feringa BL. Recl. Trav. Chim. Pays-Bas 1987; 106: 469
10d Cottier L, Descotes G, Eymard L, Rapp K. Synthesis 1995; 303
10e Annangudi SP, Sun MJ, Salomon RG. Synlett 2005; 1468

11a Larson RT, Pemberton RP, Franke JM, Tantillo DJ, Thomson RJ. J. Am. Chem. Soc. 2015; 137: 11197
11b Chackalamannil S, Wang YG, Greenlee WJ, Hu ZY, Xia Y, Ahn HS, Boykow G, Hsieh YS, Palamanda J, Agans-Fantuzzi J, Kurowski S, Graziano M, Chintala M. J. Med. Chem. 2008; 51: 3061

12 Liu P, Pan YM, Hu K, Huang XC, Liang Y, Wang HS. Tetrahedron 2013; 69: 7925
13 Miles WH, Duca DG, Selfridge BR, De Sousa CA. P, Harriman KB, Goodzeit EO, Freedman JT. Tetrahedron Lett. 2007; 48: 7809
14 In some cases, broadening of the peaks in the NMR spectra of these cycloadducts may be attributable to hydrogen bonding; see: Klika KD, Tahtinen P, Dahlqvist M, Szabo JA, Stajer G, Sinkkonen J, Pihlaja K. J. Chem. Soc., Perkin Trans. 2 2000; 687

For representative examples of isomerization of [2.2.1]-bicyclic systems, see:

15a Suzuki J, Harada T. Synthesis 2006; 2483
15b Miklos F, Sohar P, Csampai A, Sillanpaa R, Peter M, Stajer G. Heterocycles 2002; 57: 2309
15c Rajsfus DE, Alter-Zilberfarb S, Frimer AA. J. Fluorine Chem. 2013; 148: 49

16 With the unequivocal synthesis of 3a and these isomerization studies, the lack of certainty about the assignment of the stereochemistry of compound ‘4’ in Pinnick’s paper is clarified.¹⁷ In Pinnick’s study, the addition of lithium dimethylcuprate to endo-Diels–Alder product of cyclopentadiene and maleic anhydride gave a product whose NMR spectra match the spectra of 12a, and not 3a. A similar study by Walton, in which cadmium reagents were added to above endo-Diels–Alder product, appears to lead to isomerization since the melting points of both 3a and 3b differ considerably from the values given in the paper but are very close to the melting points found for isomerized compounds 12a and 12b.¹⁸ A study of the addition of some Grignard reagents to anhydrides has previously been noted to cause isomerization of the resulting keto acids.¹⁹ The nickel-catalyzed reactions of zinc reagents to anhydrides, on the other hand, appears to occur without isomerization, since the product from the above endo-Diels–Alder product exhibited a complex ¹H NMR spectra due to ‘rotomers,’ that is, ring and chain tautomers.²⁰
17 Cornelius LA. M, Bone RG. A, Hastings RH, Deardorff MA, Scharlach RA, Hauptmann BE, Stankovic CS, Pinnick HW. J. Org. Chem. 1993; 58: 3188
18 Walton HM. J. Org. Chem. 1957; 22: 312
19 Canonne P, Plamondon J, Akssira M. Tetrahedron 1988; 44: 2903
20 Bercot EA, Rovis T. J. Am. Chem. Soc. 2002; 124: 174
21 Rinner U, Lentsch C, Aichinger C. Synthesis 2010; 3763
22 Chackalamannil S, Wang YG, Greenlee WJ, Hu ZY, Xia Y, Ahn HS, Boykow G, Hsieh YS, Palamanda J, Agans-Fantuzzi J, Kurowski S, Graziano M, Chintala M. J. Med. Chem. 2008; 51: 3061
23 Gao LJ, Waelbroeck M, Hofman S, Van Haver D, Milanesio M, Viterbo D, De Clercq PJ. Bioorg. Med. Chem. Lett. 2002; 12: 1909
24 Doller D, Chackalamannil S, Czarniecki M, McQuade R, Ruperto V. Bioorg. Med. Chem. Lett. 1999; 9: 901
25 Larson RT, Pemberton RP, Franke JM, Tantillo DJ, Thomson RJ. J. Am. Chem. Soc. 2015; 137: 11197
26 Howell JM, Liu W, Young AJ, White MC. J. Am. Chem. Soc. 2006; 136: 5750
27 Takadoi M, Katoh T, Ishiwata A, Terashima S. Tetrahedron 2002; 58: 9903
28 Takadoi M, Yamaguchi K, Terashima S. Bioorg. Med. Chem. 2003; 11: 1169
29 Bercot EA, Kindrachuk DE, Rovis T. Org. Lett. 2005; 7: 107

30a Shi H, Liu H, Bloch R, Mandville GR. Tetrahedron 2001; 57: 9335
30b Frenette R, Monette M, Bernstein MA, Young RN, Verhoeven TR. J. Org. Chem. 1991; 56: 3083

31 APEX2 . Bruker AXS Inc; Madison (WI, USA): 2009
32 Sheldrick GM. SADABS . University of Gottingen; Germany: 2008
33 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
34 Allen FH, Johnson O, Shields GP, Smith BR, Towler M. J. Appl. Crystallogr. 2004; 37: 335
35 Cycloadduct 9e has been previously reported, but likely to be the trans-compound: Andreev VM, Usova AV. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1966; 15: 1351

Supplementary Material

Supporting Information