Synthesis of (S,5Z,8E,10E)-12-Hydroxyheptadeca-5,8,10-trienoic Acid (12S-HHT) and its Analogues

Toshifumi Tojo; Qian Wang; Toshiaki Okuno; Takehiko Yokomizo; Yuichi Kobayashi

doi:10.1055/s-0033-1338961

Synlett, Table of Contents

Synlett 2013; 24(12): 1545-1548
DOI: 10.1055/s-0033-1338961

letter

Synthesis of (S,5Z,8E,10E)-12-Hydroxyheptadeca-5,8,10-trienoic Acid (12S-HHT) and its Analogues

Authors

Toshifumi Tojo

^aDepartment of Bioengineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan Fax: +81(45)9245789 Email: ykobayas@bio.titech.ac.jp
Qian Wang

^aDepartment of Bioengineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan Fax: +81(45)9245789 Email: ykobayas@bio.titech.ac.jp
Toshiaki Okuno

^bDepartment of Biochemistry, Juntendo University School of Medicine, Hongo 2-1-1, Bunkyo-ku, Tokyo 113-8421, Japan
Takehiko Yokomizo

^bDepartment of Biochemistry, Juntendo University School of Medicine, Hongo 2-1-1, Bunkyo-ku, Tokyo 113-8421, Japan
Yuichi Kobayashi*

^aDepartment of Bioengineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan Fax: +81(45)9245789 Email: ykobayas@bio.titech.ac.jp

Abstract

All articles of this category

Abstract

Natural 12S-HHT and its analogues were synthesized for study of structure and activity relationship toward the BLT2 receptor. The Suzuki–Miyaura coupling was used for construction of the 8E,10E-diene moiety of 12S-HHT and analogues of (12R)- and 12-keto-types, whereas Wittig reaction was used for the synthesis of (8Z)- and (8Z,12R)-isomers.

Key words

asymmetric synthesis - cross-coupling - HHT - Wittig reaction - Suzuki–Miyaura coupling

Full Text

References

References and Notes

1a Yokomizo T. Adv. Enzyme Regul. 2011; 51: 59
1b Brink C, Dahlén S.-E, Drazen J, Evans JF, Hay DW. P, Nicosia S, Serhan CN, Shimizu T, Yokomizo T. Pharmacol. Rev. 2003; 55: 195
1c Tager AM, Luster AD. Prostaglandins Leukotrienes Essent. Fatty Acids 2003; 69: 123

2a Yokomizo T, Izumi T, Chang K, Takuwa Y, Shimizu T. Nature 1997; 387: 620
2b Yokomizo T, Kato K, Terawaki K, Izumi T, Shimizu T. J. Exp. Med. 2000; 192: 421

3 Okuno T, Iizuka Y, Okazaki H, Yokomizo T, Taguchi R, Shimizu T. J. Exp. Med. 2008; 205: 759

4a Iizuka Y, Yokomizo T, Terawaki K, Komine M, Tamaki K, Shimizu T. J. Biol. Chem. 2005; 280: 24816
4b Yasuda D, Okuno T, Yokomizo T, Hori T, Hirota N, Hashidate T, Miyano M, Shimizu T, Nakamura M. FASEB J. 2009; 23: 1470
4c Iizuka Y, Okuno T, Saeki K, Uozaki H, Okada S, Misaka M, Sato T, Toh H, Fukayama M, Takeda N, Kita Y, Shimizu T, Nakamura A, Yokomizo T. FASEB J. 2010; 24: 4678

5a Hamberg M, Samuelsaon B. Proc. Natl. Acad. Sci. U.S.A. 1974; 71: 3400
5b Hamberg M, Svensson J, Samuelsson B. Proc. Natl. Acad. Sci. U.S.A. 1974; 71: 3824
5c Shimizu T, Kondo K, Hayaishi O. Arch. Biochem. Biophys. 1981; 206: 271

6a Suzuki M, Noyori R. J. Am. Chem. Soc. 1982; 104: 2024
6b Suzuki M, Ohtake H, Kameya Y, Hamanaka N, Noyori R. J. Org. Chem. 1989; 54: 5292
6c Russell SW, Pabon HJ. J. J. Chem. Soc., Perkin Trans. 1 1982; 545
6d Greé R, Tourbah H, Carrié R. Tetrahedron Lett. 1986; 27: 4983
6e De Montarby L, Tourbah H, Greé R. Bull. Chim. Soc. Fr. 1989; 419
6f Nicolaou KC, Stylianides NA, Ramphal JY. J. Chem. Soc., Perkin Trans. 1 1989; 2131

7a Agins A, Thomas MJ, Edmonds CG, McCloskey JA. Biochem. Pharmacol. 1987; 36: 1799
7b Liu Y, Yoden K, Shen R.-F, Tai H.-H. Biochem. Biophys. Res. Commun. 1985; 129: 268

8a Ogawa N, Kobayashi Y. Tetrahedron Lett. 2009; 50: 6079
8b Kosaki Y, Ogawa N, Kobayashi Y. Tetrahedron Lett. 2010; 51: 1856
8c Ogawa N, Kobayashi Y. Tetrahedron Lett. 2011; 52: 3001

9a Gao Y, Klunder JM, Hanson RM, Ko SY, Masamune H, Sharpless KB. J. Am. Chem. Soc. 1987; 109: 5765
9b Kitano Y, Matsumoto T, Sato F. Tetrahedron 1988; 44: 4073

10 Matsumura K, Hashiguchi S, Ikariya T, Noyori R. J. Am. Chem. Soc. 1997; 119: 8738
11 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
12 Kitano Y, Matsumoto T, Wakasa T, Okamoto S, Shimazaki T, Kobayashi Y, Sato F. Tetrahedron Lett. 1987; 28: 6351
13 The Noyori reduction of acetylene ketone i afforded alcohol ii with 96% ee by chiral HPLC of the derived benzoate. However, hydrostannation of the TBDPS ether iii under radical- (AIBN) or PdCl₂(PPh₃)₂-catalyzed conditions followed by iodination gave a mixture of (S)-7, the cis-isomer, and the regioisomer (Scheme 3).
14 12S-HHT (1): ¹H NMR (300 MHz, CDCl₃): δ = 0.90 (t, J = 7.0 Hz, 3 H), 1.14–1.80 (m, 10 H), 2.00–2.20 (m, 2 H), 2.37 (t, J = 7.5 Hz, 2 H), 2.83 (t, J = 6.0 Hz, 2 H), 2.60–4.00 (br s, 2 H), 4.12 (q, J = 6.0 Hz, 1 H), 5.30–5.52 (m, 2 H), 5.55–5.73 (m, 2 H), 6.04 (dd, J = 15.0, 10.5 Hz, 1 H), 6.18 (dd, J = 15.0, 10.5 Hz, 1 H). (8Z)-Isomer 3: ¹H NMR (300 MHz, CDCl₃): δ = 0.91 (t, J = 7.0 Hz, 3 H), 1.18–1.81 (m, 10 H), 2.00–2.26 (m, 2 H), 2.36 (t, J = 7.0 Hz, 2 H), 2.87 (dt, J = 16.0, 7.0 Hz, 1 H), 3.03 (dt, J = 16.0, 7.0 Hz, 1 H), 3.20–4.00 (br s, 2 H), 4.26 (q, J = 6.0 Hz, 1 H), 5.32–5.52 (m, 3 H), 5.69 (dd, J = 15.0, 6.0 Hz, 1 H), 5.98 (t, J = 11.0 Hz, 1 H), 6.58 (dd, J = 15.0, 11.0 Hz, 1 H). 12-Keto isomer 5: ¹H NMR (300 MHz, CDCl₃): δ = 0.91 (t, J = 7.0 Hz, 3 H), 1.23–1.42 (m, 5 H), 1.57–1.82 (m, 4 H), 2.08–2.22 (m, 2 H), 2.38 (t, J = 7.0 Hz, 2 H), 2.55 (t, J = 7.5 Hz, 2 H), 2.94 (t, J = 5.0 Hz, 2 H), 5.40–5.55 (m, 2 H), 6.05–6.26 (m, 3 H), 7.13 (dd, J = 16.0, 10.0 Hz, 1 H).

15a Nikas SP, D’Souza M, Makriyannis A. Tetrahedron 2012; 68: 6329
15b Rao AV. R, Purandare AV, Singh AK. Bioorg. Med. Chem. Lett. 1991; 1: 201
15c Gunn BP, Brooks DW. J. Org. Chem. 1985; 50: 4417