Synlett 2020; 31(05): 421-433
DOI: 10.1055/s-0039-1691580
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© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions

,
Akihiro Ogura
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan   Email: takao@applc.keio.ac.jp
,
Keisuke Yoshida
,
Siro Simizu
› Author Affiliations
This work was supported by the MEXT-Supported Program for the Strategic Research Foundation at Private Universities, 2012–2016, Japan Society for the Promotion of Science (JSPS), Grants-in-Aid for Scientific Research (KAKENHI) (Grant Nos. 15750094 and 15K05504) from Japan Society for the Promotion of Science (JSPS), the Naito Foundation, and the Keio Gijuku Academic Development Funds.
Further Information

Publication History

Received: 08 December 2019

Accepted after revision: 29 December 2019

Publication Date:
03 February 2020 (online)


Abstract

In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.

1 Introduction

2 Total Synthesis of (+)-Pestalotiopsin A

3 Total Synthesis of (+)-Cytosporolide A

4 Total Synthesis of (+)-Vibsanin A

5 Total Syntheses of (+)-Aquatolide and Related Humulanolides

6 Conclusion

 
  • References

  • 1 Current address: Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan.
    • 2a Okude Y, Hirano S, Hiyama T, Nozaki H. J. Am. Chem. Soc. 1977; 99: 3179
    • 2b Takai K, Kimura K, Kuroda T, Hiyama T, Nozaki H. Tetrahedron Lett. 1983; 24: 5281
    • 2c Jin H, Uenishi J, Christ WJ, Kishi Y. J. Am. Chem. Soc. 1986; 108: 5644
    • 2d Takai K, Tagashira M, Kuroda T, Oshima K, Utimoto K, Nozaki H. J. Am. Chem. Soc. 1986; 108: 6048
    • 2e For a review on the NHTK reaction in natural products synthesis, see: Gil A, Albericio F, Álvarez M. Chem. Rev. 2017; 117: 8420
    • 3a Takao K, Hayakawa N, Yamada R, Yamaguchi T, Morita U, Kawasaki S, Tadano K. Angew. Chem. Int. Ed. 2008; 47: 3426
    • 3b Takao K, Hayakawa N, Yamada R, Yamaguchi T, Saegusa H, Uchida M, Samejima S, Tadano K. J. Org. Chem. 2009; 74: 6452
  • 4 Takao K, Noguchi S, Sakamoto S, Kimura M, Yoshida K, Tadano K. J. Am. Chem. Soc. 2015; 137: 15971
  • 5 Takao K, Tsunoda K, Kurisu T, Sakama A, Nishimura Y, Yoshida K, Tadano K. Org. Lett. 2015; 17: 756
  • 6 Takao K, Kai H, Yamada A, Fukushima Y, Komatsu D, Ogura A, Yoshida K. Angew. Chem. Int. Ed. 2019; 58: 9851
  • 7 Pulici M, Sugawara F, Koshino H, Uzawa J, Yoshida S, Lobkovsky E, Clardy J. J. Org. Chem. 1996; 61: 2122 ; addition/correction: J. Org. Chem. 1997, 62, 1564
    • 8a Corey EJ, Mitra RB, Uda H. J. Am. Chem. Soc. 1963; 85: 362
    • 8b Corey EJ, Mitra RB, Uda H. J. Am. Chem. Soc. 1964; 86: 485
  • 9 Ohtsuka Y, Niitsuma S, Tadokoro H, Hayashi T, Oishi T. J. Org. Chem. 1984; 49: 2326

    • For synthetic studies of pestalotiopsin A, see:
    • 10a Johnston D, Francon N, Edmonds DJ, Procter DJ. Org. Lett. 2001; 3: 2001
    • 10b Johnston D, Couché E, Edmonds DJ, Muir KW, Procter DJ. Org. Biomol. Chem. 2003; 1: 328
    • 10c Edmonds DJ, Muir KW, Procter DJ. J. Org. Chem. 2003; 68: 3190
    • 10d Baker TM, Edmonds DJ, Hamilton D, O’Brien CJ, Procter DJ. Angew. Chem. Int. Ed. 2008; 47: 5631
    • 10e Paquette LA, Cunière N. Org. Lett. 2002; 4: 1927
    • 10f Paquette LA, Kang H.-J. Tetrahedron 2004; 60: 1353
    • 10g Paquette LA, Parker GD, Tei T, Dong S. J. Org. Chem. 2007; 72: 7125 ; addition/correction: J. Org. Chem. 2009, 74, 1812
    • 10h Paquette LA, Dong S, Parker GD. J. Org. Chem. 2007; 72: 7135
    • 10i Dong S, Paquette LA. Heterocycles 2007; 72: 111
    • 10j Maulide N, Markó IE. Chem. Commun. 2006; 1200
  • 11 Takao K, Saegusa H, Tsujita T, Washizawa T, Tadano K. Tetrahedron Lett. 2005; 46: 5815
  • 12 Li Y, Niu S, Sun B, Liu S, Liu X, Che Y. Org. Lett. 2010; 12: 3144
  • 13 Spence JT. J, George JH. Org. Lett. 2011; 13: 5318
  • 14 Smetanina OF, Kuznetsova TA, Gerasimenko AV, Kalinovsky AI, Pivkin MV, Dmitrenok PC, Elyakov GB. Russ. Chem. Bull. 2004; 53: 2643
  • 15 Inagaki T, Kaneda K, Suzuki Y, Hirai H, Nomura E, Sakakibara T, Yamauchi Y, Huang LH, Norcia M, Wondrack LM, Sutcliffe JA, Kojima N. J. Antibiot. 1998; 51: 112
  • 16 Otake K, Yamada K, Miura K, Sasazawa Y, Miyazaki S, Niwa Y, Ogura A, Takao K, Simizu S. Bioorg. Med. Chem. 2019; 27: 3334
  • 17 Kawazu K. Agric. Biol. Chem. 1980; 44: 1367
  • 18 Fukuyama Y, Kubo M, Esumi T, Harada K, Hioki H. Heterocycles 2010; 81: 1571
  • 19 Takao K, Miyashita T, Akiyama N, Kurisu T, Tsunoda K, Tadano K. Heterocycles 2012; 86: 147
  • 20 Sakama A, Nishimura Y, Motohashi Y, Yoshida K, Takao K. Tetrahedron 2016; 72: 5465
  • 21 Takai K, Nitta K, Utimoto K. J. Am. Chem. Soc. 1986; 108: 7408
  • 22 Yu Z.-Y, Xiao H, Wang L.-M, Shen X, Jing Y, Wang L, Sun W.-F, Zhang Y.-F, Cui Y, Shan Y.-J, Zhou W.-B, Xing S, Xiong G.-L, Liu X.-L, Dong B, Feng J.-N, Wang L.-S, Luo Q.-L, Zhao Q.-S, Cong Y.-W. Cancer Res. 2016; 76: 2698
  • 23 Matsuki W, Miyazaki S, Yoshida K, Ogura A, Sasazawa Y, Takao K, Simizu S. Bioorg. Med. Chem. Lett. 2017; 27: 4536
  • 24 Miura K, Matsuki W, Ogura A, Takao K, Simizu S. Bioorg. Med. Chem. 2020; 28: 115253
  • 25 San Feliciano A, Medarde M, Miguel del Corral JM, Aramburu A, Gordaliza M, Barrero AF. Tetrahedron Lett. 1989; 30: 2851
  • 26 Lodewyk MW, Soldi C, Jones PB, Olmstead MM, Rita J, Shaw JT, Tantillo DJ. J. Am. Chem. Soc. 2012; 134: 18550
    • 27a San Feliciano A, Barrero AF, Medarde M, Miguel del Corral JM, Ledesma E, Sánchez-Ferrando F. Tetrahedron Lett. 1982; 23: 3097
    • 27b San Feliciano A, Barrero AF, Medarde M, Miguel del Corral JM, Aramburu Aizpiri A, Sánchez-Ferrando F. Tetrahedron 1984; 40: 873
    • 27c San Feliciano A, Barrero AF, Medarde M, Miguel del Corral JM, Aramburu A, Perales A, Fayos J, Sánchez-Ferrando F. Tetrahedron 1985; 41: 5711
    • 28a Takao K, Nanamiya R, Fukushima Y, Namba A, Yoshida K, Tadano K. Org. Lett. 2013; 15: 5582
    • 28b Takao K, Nemoto R, Mori K, Namba A, Yoshida K, Ogura A. Chem. Eur. J. 2017; 23: 3828
    • 28c Takao K, Mori K, Kasuga K, Nanamiya R, Namba A, Fukushima Y, Nemoto R, Mogi T, Yasui H, Ogura A, Yoshida K, Tadano K. J. Org. Chem. 2018; 83: 7060
    • 28d Miyazaki S, Sasazawa Y, Mogi T, Suzuki T, Yoshida K, Dohmae N, Takao K, Simizu S. FEBS Lett. 2016; 590: 1163
    • 29a Trost BM, Burns AC, Bartlett MJ, Tautz T, Weiss AH. J. Am. Chem. Soc. 2012; 134: 1474
    • 29b Han J.-C, Li F, Li C.-C. J. Am. Chem. Soc. 2014; 136: 13610
    • 30a Saya JM, Vos K, Kleinnijenhuis RA, van Maarseveen JH, Ingemann S, Hiemstra H. Org. Lett. 2015; 17: 3892
    • 30b Wang B, Xie Y, Yang Q, Zhang G, Gu Z. Org. Lett. 2016; 18: 5388
    • 31a Srinivasan R, Carlough KH. J. Am. Chem. Soc. 1967; 89: 4932
    • 31b Liu RS. H, Hammond GS. J. Am. Chem. Soc. 1967; 89: 4936
  • 32 Hammoud L, León F, Brouard I, Gonzalez-Platas J, Benayache S, Mosset P, Benayache F. Tetrahedron Lett. 2018; 59: 2668
  • 33 El Dahmy S, Jakupovic J, Bohlmann F, Sarg TM. Tetrahedron 1985; 41: 309