Total Synthesis of (+)-Fostriecin
and (+)-Phoslactomycin B

Setsuya Shibahara; Masataka Fujino; Yasumasa Tashiro; Nanako Okamoto; Tomoyuki Esumi; Keisuske Takahashi; Jun Ishihara; Susumi Hatakeyama

doi:10.1055/s-0029-1216930

PAPER

Total Synthesis of (+)-Fostriecin and (+)-Phoslactomycin B

Setsuya Shibahara, Masataka Fujino, Yasumasa Tashiro, Nanako Okamoto, Tomoyuki Esumi, Keisuske Takahashi, Jun Ishihara, Susumi Hatakeyama*
Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan
Fax: +81(95)8192426; e-Mail: susumi@nagasaki-u.ac.jp;

Abstract

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Abstract

(+)-Fostriecin and (+)-phoslactomycin B, which are potent and selective inhibitors of protein phosphatase, were synthesized by a highly enantio- and stereoselective approach that enabled us to prepare all possible isomers at both the C11 secondary alcohol position and the Δ^¹²-double bond.

Key words

antibiotics - fostriecin - phoslactomycin - total synthesis

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References

<A NAME="RC01809SS-1A">1a</A> Tunac JB. Graham BD. Dobson WE. J. Antibiot. 1983, 36: 1595

<A NAME="RC01809SS-1B">1b</A> Stampwala SS. Bunge RH. Hurley TR. Willmer NE. Brankiewicz AJ. Steinman CE. Smitka TA. French JC. J. Antibiot. 1983, 36: 1601

<A NAME="RC01809SS-1C">1c</A> Boger DL. Hikota M. Lewis BM. J. Org. Chem. 1997, 62: 1748

<A NAME="RC01809SS-2A">2a</A> Fushimi S. Nishikawa S. Shimizu A. Seto H. J. Antibiot. 1989, 42: 1019

<A NAME="RC01809SS-2B">2b</A> Fushimi S. Furihata K. Seto H. J. Antibiot. 1989, 42: 1026

<A NAME="RC01809SS-2C">2c</A> Ozasa T. Suzuki K. Sasamata M. Tanaka K. Kobori M. Kadota S. Nagai K. Saito T. Watanabe S. Iwanami M. J. Antibiot. 1989, 42: 1331

<A NAME="RC01809SS-2D">2d</A> Ozasa T. Tanaka K. Sasamata M. Kaniwa H. Shimizu M. Matsumoto H. Iwanami M. J. Antibiot. 1989, 42: 1339

<A NAME="RC01809SS-2E">2e</A> Shibata T. Kurihara S. Yoda K. Haruyama H. Tetrahedron 1995, 51: 11999

<A NAME="RC01809SS-2F">2f</A> Sekiyama Y. Palaniappan N. Reynolds KA. Osada H. Tetrahedron 2003, 59: 7465

<A NAME="RC01809SS-2G">2g</A> Choudhuri SD. Ayers S. Soine WH. Reynolds KV. J. Antibiot. 2005, 58: 573

<A NAME="RC01809SS-2H">2h</A> Mizuhara N. Usuki Y. Ogita M. Fujita K. Kuroda M. Doe M. Iio H. Tanaka T. J. Antibiot. 2007, 60: 762

<A NAME="RC01809SS-3">3</A> Tomiya T. Uramoto M. Isono K. J. Antibiot. 1990, 43: 118

<A NAME="RC01809SS-4A">4a</A> Kohma T. Enokita R. Okazaki T. Miyaoka H. Torikata A. Inukai M. Kaneko I. Kagasaki T. Sakaida Y. Satoh A. Shiraishi A. J. Antibiot. 1993, 46: 1503

<A NAME="RC01809SS-4B">4b</A> Kohma T. Nakamura T. Kinoshita T. Kaneko I. Shiraishi A. J. Antibiot. 1993, 46: 1512

<A NAME="RC01809SS-5A">5a</A> Lewy DS. Gauss C.-M. Soenen DR. Boger DL. Curr. Med. Chem. 2002, 9: 2005

<A NAME="RC01809SS-5B">5b</A> Buck SB. Hardouin C. Ichikawa S. Soenen DR. Gauss C.-M. Hwang I. Swingle MR. Bonness KM. Honkanen RE. Boger DL. J. Am. Chem. Soc. 2003, 125: 15694

<A NAME="RC01809SS-6A">6a</A> Walsh AH. Cheng A. Honkanen RE. FEBS Lett. 1997, 416: 230

<A NAME="RC01809SS-6B">6b</A> Hastie CJ. Cohen PT. FEBS Lett. 1998, 431: 357

<A NAME="RC01809SS-6C">6c</A> Usui T. Marriott G. Inagaki M. Swarup G. Osada H. J. Biochem. 1999, 125: 960

<A NAME="RC01809SS-6D">6d</A> Kawada M. Kawatsu M. Masuda T. Ohba S. Amemiya M. Kohama T. Ishizuka M. Takeuuchi T. Int. Immunopharmacol. 2003, 3: 179

<A NAME="RC01809SS-6E">6e</A> Teruya T. Shimizu S. Kanoh N. Osada H. FEBS Lett. 2005, 579: 2463

<A NAME="RC01809SS-7">7</A> Palaniappan N. Kim BS. Sekiyama Y. Osada H. Reynolds KA. J. Biol. Chem. 2003, 278: 35552

For reviews, see:

<A NAME="RC01809SS-8A">8a</A> Shibasaki M. Kanai M. Heterocycles 2005, 66: 727

<A NAME="RC01809SS-8B">8b</A> Miyashita K. Ikejiri M. Tsunemi T. Matsumoto A. Imanishi T. J. Synth. Org. Chem., Jpn. 2007, 65: 874

<A NAME="RC01809SS-9A">9a</A> Boger DL. Ichikawa S. Zhong W. J. Am. Chem. Soc. 2001, 123: 4161

<A NAME="RC01809SS-9B">9b</A> Cossy J. Pradaux F. BouzBouz S. Org. Lett. 2001, 3: 2233

<A NAME="RC01809SS-9C">9c</A> Chavez DE. Jacobsen EN. Angew. Chem. Int. Ed. 2001, 40: 3667

<A NAME="RC01809SS-9D">9d</A> Reddy YK. Falck JR. Org. Lett. 2002, 4: 961

<A NAME="RC01809SS-9E">9e</A> Miyashita K. Ikejiri M. Kawasaki H. Maemura S. Imanishi T. Chem. Commun. 2002, 742

<A NAME="RC01809SS-9F">9f</A> Esumi T. Okamoto N. Hatakeyama S. Chem. Commun. 2002, 3042

<A NAME="RC01809SS-9G">9g</A> Wang Y.-G. Kobayashi Y. Org. Lett. 2002, 4: 4615

<A NAME="RC01809SS-9H">9h</A> Miyashita K. Ikejiri M. Kawasaki H. Maemura S. Imanishi T. J. Am. Chem. Soc. 2003, 125: 8238

<A NAME="RC01809SS-9I">9i</A> Fujii K. Maki K. Kanai M. Shibasaki M. Org. Lett. 2003, 5: 733

<A NAME="RC01809SS-9J">9j</A> Maki K. Motoki R. Fujii K. Kanai M. Kobayashi T. Tamura S. Shibasaki M. J. Am. Chem. Soc. 2005, 127: 17111

<A NAME="RC01809SS-9K">9k</A> Trost BM. Frederiksen MU. Papillon JPN. Harrington PE. Shin S. Shireman BT. J. Am. Chem. Soc. 2005, 127: 3666

<A NAME="RC01809SS-9L">9l</A> Yadav JS. Prathap I. Tadai BP. Tetrahedron Lett. 2006, 47: 3773

<A NAME="RC01809SS-9M">9m</A> Hayashi Y. Yamaguchi H. Toyoshima M. Okado K. Toyo T. Shoji M. Org. Lett. 2008, 10: 1405

<A NAME="RC01809SS-10">10</A> Takeuchi T. Kuramochi K. Kobayashi S. Sugawara F. Org. Lett. 2006, 8: 5307

<A NAME="RC01809SS-11">11</A> Shimada K. Kabburagi Y. Fukuyama T. J. Am. Chem. Soc. 2003, 125: 4048

<A NAME="RC01809SS-12A">12a</A> Miyashita K. Tsunemi T. Hosokawa T. Ikejiri M. Imanishi T. Tetrahedron Lett. 2007, 48: 3829

<A NAME="RC01809SS-12B">12b</A> Miyashita K. Tsunemi T. Hosokawa T. Ikejiri M. Imanishi T. J. Org. Chem. 2008, 73: 5360

<A NAME="RC01809SS-12C">12c</A> Moïse J. Sonawane RP. Corsi C. Wendeborn SV. Arseniyadis S. Cossy J. Synlett 2008, 2617

<A NAME="RC01809SS-13A">13a</A> Wang Y.-G. Takeyama T. Kobayashi Y. Angew. Chem. Int. Ed. 2006, 45: 3320

<A NAME="RC01809SS-13B">13b</A> Nonaka H. Maeda N. Kobayashi Y. Tetrahedron Lett. 2007, 48: 5601

<A NAME="RC01809SS-13C">13c</A> Shibahara S. Fujino M. Tashiro Y. Takahashi K. Ishihara J. Hatakeyama S. Org. Lett. 2008, 10: 2139

<A NAME="RC01809SS-13D">13d</A> Druais V. Hall MJ. Corsi C. Wendeborn SV. Meyer C. Cossy J. Org. Lett. 2009, 11: 935

<A NAME="RC01809SS-13E">13e</A> König C. M. Gebhardt B. Schleth C. Dauber M. Koert U. Org. Lett. 2009, 11: 2728

<A NAME="RC01809SS-14">14</A> Taniguchi M. Kobayashi S. Nakagawa M. Hino T. Kishi Y. Tetrahedron Lett. 1986, 27: 4763

<A NAME="RC01809SS-15">15</A> For a review on syn- and anti-selective reductions of β-hydroxy ketones, see: Greeves N. In Comprehensive Organic Synthesis Vol. 8: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.1

For reviews, see:

<A NAME="RC01809SS-16A">16a</A> Schuster M. Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36: 2036

<A NAME="RC01809SS-16B">16b</A> Grubbs RH. Chang S. Tetrahedron 1998, 54: 4413

<A NAME="RC01809SS-17">17</A> For a review, see: Kolb HC. Van Nieuwenhze MS. Sharpless KB. Chem. Rev. 1994, 94: 2483

<A NAME="RC01809SS-18">18</A> Fargeas V. Ménez PL. Berque I. Aldisson J. Panctazi A. Tetrahedron 1996, 52: 6613

<A NAME="RC01809SS-19">19</A> Jeffry T. Tetrahedron Lett. 1985, 26: 2667

<A NAME="RC01809SS-20">20</A> Jadav PK. Bhat KS. Perumal PT. Brown HC. J. Org. Chem. 1986, 51: 432

<A NAME="RC01809SS-21">21</A> Ghosh AK. Cappiello J. Shin D. Tetrahedron Lett. 1998, 39: 4651

<A NAME="RC01809SS-22">22</A> For site-selective asymmetric dihydroxylation of polyenes, see: Becker H. Soler MA. Sharpless KB. Tetrahedron 1995, 51: 1345

<A NAME="RC01809SS-23">23</A> Evans DA. Chapman T. Carreira EM. J. Am. Chem. Soc. 1988, 110: 3560

<A NAME="RC01809SS-24">24</A> Chen K.-M. Hardtmann GE. Prasad K. Repic O. Shapiro MJ. Tetrahedron Lett. 1987, 28: 155

<A NAME="RC01809SS-25">25</A> Stille JK. Groh BL. J. Am. Chem. Soc. 1987, 109: 813

<A NAME="RC01809SS-26">26</A> Mapp AK. Heathcock CH. J. Org. Chem. 1999, 64: 23

<A NAME="RC01809SS-27">27</A> Bannwarth W. Trzeciak A. Helv. Chim. Acta 1987, 70: 175

<A NAME="RC01809SS-28A">28a</A> Hayakawa Y. Kato H. Uchiyama M. Kajino H. Noyori R. J. Org. Chem. 1986, 51: 2400

<A NAME="RC01809SS-28B">28b</A> Hayakawa Y. Wakabayashi S. Nobori T. Noyori R. Tetrahedron Lett. 1987, 28: 2259

For reviews, see:

<A NAME="RC01809SS-29A">29a</A> Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

<A NAME="RC01809SS-29B">29b</A> Suzuki A. J. Organomet. Chem. 1999, 576: 147

<A NAME="RC01809SS-30A">30a</A> Brown HC. Bhat KS. J. Am. Chem. Soc. 1986, 108: 293

<A NAME="RC01809SS-30B">30b</A> Roush WR. Ando K. Powers DB. Palkowitz AD. Halterman RL. J. Am. Chem. Soc. 1990, 112: 6339

<A NAME="RC01809SS-31">31</A> Roush WR. Ando K. Powers DB. Palkowitz AD. Halterman RL. J. Am. Chem. Soc. 1990, 112: 6339

<A NAME="RC01809SS-32">32</A> After our report,^¹4c the following papers appeared: Sonawane RP. Joolakanti SR. Arseniyadis S. Cossy J. Synlett 2009, 213 ; and reference 13c

<A NAME="RC01809SS-33A">33a</A> Braun NA. Klein I. Spitzner D. Vogler B. Braun S. Borrmann H. Simon A. Liebigs Ann. 1995, 2165

<A NAME="RC01809SS-33B">33b</A> Moreau X. Campagne J.-M. J. Org. Chem. 2003, 68: 5346

<A NAME="RC01809SS-34">34</A> Kamatani A. Overman LE. J. Org. Chem. 1999, 64: 8743

<A NAME="RC01809SS-35">35</A> Nicolaou KC. Yue EW. Naniwa Y. Riccardis FD. Nadin A. Leresche JE. Greca SL. Yang Z. Angew. Chem., Int. Ed. Engl. 1994, 33: 2187

<A NAME="RC01809SS-36">36</A> Rodriguez A. Nomen M. Spur BW. Godfroid JJ. Tetrahedron Lett. 1999, 40: 5161