Stereo- and Regioselective Synthesis of (E,E)-Dienes: Evolution from the Transition-Metal-Catalyzed Cross-Coupling to Titanium Alkoxide-Based Alkyne–Alkyne Reductive Coupling

Bin Cai; Ren Wei Toh; Hwee Ting Ang; Jie Wu; James S. Panek

doi:10.1055/a-1977-1006

Synlett, Table of Contents

Synlett 2023; 34(08): 889-911
DOI: 10.1055/a-1977-1006

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Stereo- and Regioselective Synthesis of (E,E)-Dienes: Evolution from the Transition-Metal-Catalyzed Cross-Coupling to Titanium Alkoxide-Based Alkyne–Alkyne Reductive Coupling

Authors

Bin Cai

^aDepartment of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston, MA 02215, USA
Ren Wei Toh

^bDepartment of Chemistry, National University of Singapore, Singapore, R. of Singapore
Hwee Ting Ang

^bDepartment of Chemistry, National University of Singapore, Singapore, R. of Singapore
Jie Wu∗

^bDepartment of Chemistry, National University of Singapore, Singapore, R. of Singapore
James S. Panek ∗

^aDepartment of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston, MA 02215, USA

Abstract

All articles of this category

Abstract

The pursuit of step- and atom-economy in natural product and complex molecule syntheses continuously inspires the development of synthetic methodologies. In this context, to enable efficient synthesis of (E,E)-dienes as common structural subunits in natural products, our lab has established robust protocols based on modified Negishi cross-couplings and evolved them to more concise titanium-mediated alkyne–alkyne reductive coupling. In this review, we summarize the natural product synthesis driven methodology development and their applications in the total synthesis of complex molecules, focusing on the studies from our laboratory.

1 Introduction

2 Transition-Metal-Catalyzed Cross-Coupling in Natural Product Synthesis

2.1 Synthesis of Branched Trisubstituted Conjugated Dienes by Negishi Coupling

2.2 Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Modified Negishi Coupling

2.3 Enantioselective Total Synthesis of Reveromycin B by Drouet & Theodorakis

2.4 Enantioselective Synthesis of the Protein Phosphatase Inhibitor (–)-Motuporin by Hu & Panek

2.5 Total Synthesis of (–)-Callystatin A by Langille & Panek

2.6 Total Synthesis of Brevisamide by Lee & Panek

3 Titanium Alkoxide-Mediated Reductive Coupling in Natural Product Synthesis

3.1 Titanium Alkoxide-Mediated Alkyne–Alkyne Reductive Coupling

3.2 Total Synthesis of Callystatin A by Reichard & Micalizio

3.3 Total Synthesis of (–)-Virginiamycin M₂ by Wu & Panek

3.4 Total Synthesis of Nuclear Factor of Activated T-Cells-68 (NFAT-68) by Cai & Panek

3.5 Titanium Alkoxide-Based Regioselective Alkyne–Alkyne Reductive Coupling Mediated by in situ Generated Arylamidate

4 Summary

Key words

cross-coupling - reductive coupling - (E,E)-diene - titanium alkoxide-mediated - total synthesis

Full Text

References

References
1 Burres NS, Premachandran U, Hoselton S, Cwik D, Hochlowski JE, Ye Q, Sunga GN, Karwowski JP, Jackson M, Whittern DN, McAlpine JB. J. Antibiot. (Tokyo) 1995; 48: 380
2 Delpierre GR, Eastwood FW, Gream GE, Kingston DG, Sarin PS, Todd L, Williams DH. J. Chem. Soc., Perkin Trans. 1 1966; 1653
3 Desilva ED, Williams DE, Andersen RJ, Klix H, Holmes CF. B, Allen TM. Tetrahedron Lett. 1992; 33: 1561
4 Hamill RL, Haney ME. Jr, Stamper M, Wiley PF. Antibiot Chemother (Northfield) 1961; 11: 328
5 Kobayashi M, Higuchi K, Murakami N, Tajima H, Aoki S. Tetrahedron Lett. 1997; 38: 2859
6 Micalizio GC, Hale SB. Acc. Chem. Res. 2015; 48: 663
7 Reichard HA, McLaughlin M, Chen MZ, Micalizio GC. Eur. J. Org. Chem. 2010; 3: 391
8 Shimp HL, Micalizio GC. Org. Lett. 2005; 7: 5111
9 Yoshida M, Kijima M, Akita M, Beppu T. J. Biol. Chem. 1990; 265: 17174
10 Zeng X, Qian M, Hu Q, Negishi E. Angew. Chem. Int. Ed. 2004; 43: 2259
11 Panek JS, Hu T. J. Org. Chem. 1997; 62: 4912
12 Panek JS, Hu T. J. Org. Chem. 1997; 62: 4914
13 Hu T, Panek JS. J. Org. Chem. 1999; 64: 3000
14 Hu T, Panek JS. J. Am. Chem. Soc. 2002; 124: 11368
15 Wu J, Panek JS. Angew. Chem. Int. Ed. 2010; 49: 6165
16 Wu J, Panek JS. J. Org. Chem. 2011; 76: 9900
17 Buchwald SL, Nielsen RB. J. Am. Chem. Soc. 1989; 111: 2870
18 Buchwald SL, Watson BT, Huffman JC. J. Am. Chem. Soc. 1987; 109: 2544
19 Mahandru GM, Liu G, Montgomery J. J. Am. Chem. Soc. 2004; 126: 3698
20 Mahandru GM, Liu G, Montgomery J. J. Am. Chem. Soc. 2004; 126: 15316
21 Huddleston RR, Jang HY, Krische MJ. J. Am. Chem. Soc. 2003; 125: 11488
22 Jang HY, Huddleston RR, Krische MJ. J. Am. Chem. Soc. 2004; 126: 466
23 Kong JR, Cho CW, Krische MJ. J. Am. Chem. Soc. 2005; 127: 11269
24 Komanduri V, Krische MJ. J. Am. Chem. Soc. 2006; 128: 16448
25 Itoh J, Han SB, Krische MJ. Angew. Chem. Int. Ed. 2009; 48: 6313
26 Guo YA, Lee W, Krische MJ. Chemistry 2017; 23: 2557
27 Liu P, McCarren P, Cheong PH, Jamison TF, Houk KN. J. Am. Chem. Soc. 2010; 132: 2050
28 Miller KM, Jamison TF. J. Am. Chem. Soc. 2004; 126: 15342
29 Miller KM, Luanphaisarnnont T, Molinaro C, Jamison TF. J. Am. Chem. Soc. 2004; 126: 4130
30 Patel SJ, Jamison TF. Angew. Chem. Int. Ed. 2003; 42: 1364
31 Luanphaisarnnont T, Ndubaku CO, Jamison TF. Org. Lett. 2005; 7: 2937
32 Moslin RM, Miller-Moslin K, Jamison TF. Chem. Commun. 2007; 4441
33 Miller KM, Huang WS, Jamison TF. J. Am. Chem. Soc. 2003; 125: 3442
34 Hamada T, Suzuki D, Urabe H, Sato F. J. Am. Chem. Soc. 1999; 121: 7342
35 Tanaka R, Hirano S, Urabe H, Sato F. Org. Lett. 2003; 5: 67
36 Perez LJ, Shimp HL, Micalizio GC. J. Org. Chem. 2009; 74: 7211
37 Bahadoor AB, Flyer A, Micalizio GC. J. Am. Chem. Soc. 2005; 127: 3694
38 Reichard HA, Micalizio GC. Angew. Chem. Int. Ed. 2007; 46: 1440
39 Reichard HA, Micalizio GC. Chem. Sci. 2011; 4: 573
40 Greszler SN, Reichard HA, Micalizio GC. J. Am. Chem. Soc. 2012; 134: 2766
41 Jeso V, Aquino C, Cheng X, Mizoguchi H, Nakashige M, Micalizio GC. J. Am. Chem. Soc. 2014; 136: 8209
42 Cai B, Evans RW, Wu J, Panek JS. Org. Lett. 2016; 18: 4304
43 Cai B, Panek JS. J. Am. Chem. Soc. 2020; 142: 3729
44 Wu J, Pu Y, Panek JS. J. Am. Chem. Soc. 2012; 134: 18440
45 Ryan J, Micalizio GC. J. Am. Chem. Soc. 2006; 128: 2764
46 Masse CE, Panek JS. Chem. Rev. 1995; 95: 1293
47 Huang HB, Panek JS. J. Am. Chem. Soc. 2000; 122: 9836
48 Huang HB, Spande TF, Panek JS. J. Am. Chem. Soc. 2003; 125: 626
49 Panek JS, Yang M. J. Am. Chem. Soc. 1991; 113: 9868
50 Jain NF, Takenaka N, Panek JS. J. Am. Chem. Soc. 1996; 118: 12475
51 Hu T, Takenaka N, Panek JS. J. Am. Chem. Soc. 2002; 124: 12806
52 Wrona IE, Gabarda AE, Evano G, Panek JS. J. Am. Chem. Soc. 2005; 127: 15026
53 Brawn RA, Panek JS. Org. Lett. 2007; 9: 2689
54 Lee J, Panek JS. Org. Lett. 2011; 13: 502
55 Wu J, Chen Y, Panek JS. Org. Lett. 2010; 12: 2112
56 Vanhorn DE, Negishi E. J. Am. Chem. Soc. 1978; 100: 2252
57 Negishi EO. N, King AO, Van Horn DE, Spiegel BI. J. Am. Chem. Soc. 1978; 100: 2254
58 Hart DW, Blackburn TF, Schwartz J. J. Am. Chem. Soc. 1975; 97: 679
59 Schwartz J, Labinger JA. Angew. Chem., Int. Ed. Engl. 1976; 15: 333
60 Drouet KE, Theodorakis EA. J. Am. Chem. Soc. 1999; 121: 456
61 Drouet KE, Theodorakis EA. Chem. Eur. J. 2000; 6: 1987
62 Coery EJ, Fuchs PL. Tetrahedron Lett. 1972; 13: 3769
63 Takai K, Nitta K, Utimoto K. J. Am. Chem. Soc. 1986; 108: 7408
64 Valentekovich RJ, Schreiber SL. J. Am. Chem. Soc. 1995; 117: 9069
65 Langille NF, Panek JS. Org. Lett. 2004; 6: 3203
66 Lee J, Panek JS. Org. Lett. 2009; 11: 4390
67 Reichard HA, Rieger JC, Micalizio GC. Angew. Chem. Int. Ed. 2008; 47: 7837
68 Dossetter AG, Jamison TF, Jacobsen EN. Angew. Chem. Int. Ed. 1999; 38: 2398
69 Lowe JT, Panek JS. Org. Lett. 2008; 10: 3813
70 Li Q, Seiple IB. J. Am. Chem. Soc. 2017; 139: 13304
71 Li Q, Seiple IB. Tetrahedron 2019; 75: 3309
72 Frantz DE, Fassler R, Carreira EM. J. Am. Chem. Soc. 2000; 122: 1806
73 Brawn RA, Panek JS. Org. Lett. 2009; 11: 4362
74 Brawn RA, Panek JS. Org. Lett. 2009; 11: 473
75 Brawn RA, Panek JS. Org. Lett. 2010; 12: 4624
76 Brawn RA, Welzel M, Lowe JT, Panek JS. Org. Lett. 2010; 12: 336
77 Leitch DC, Beard JD, Thomson RK, Wright VA, Patrick BO, Schafer LL. Eur. J. Inorg. Chem. 2009; 2691
78 Payne PR, Thomson RK, Medeiros DM, Wan G, Schafer LL. Dalton Trans. 2013; 42: 15670
79 Yim JC. H, Bexrud JA, Ayinla RO, Leitch DC, Schafer LL. J. Org. Chem. 2014; 79: 2015
80 Ryken SA, Schafer LL. Acc. Chem. Res. 2015; 48: 2576