Syntheses of the D-, E-, F-, and I-Ring Parts of Ciguatoxin by a Common Strategy Starting from Tri-O-acetyl-d-glucal

Kenshu  Fujiwara; Yasuhito  Koyama; Eriko  Doi; Ken  Shimawaki; Yuko  Ohtaniuchi; Atsushi  Takemura; Shin-ichiro  Souma; Akio  Murai

doi:10.1055/s-2002-33527

LETTER

Syntheses of the D-, E-, F-, and I-Ring Parts of Ciguatoxin by a Common Strategy Starting from Tri- O -acetyl- d -glucal

Kenshu Fujiwara*^a, Yasuhito Koyama^a, Eriko Doi^a, Ken Shimawaki^a, Yuko Ohtaniuchi^a, Atsushi Takemura, Shin-ichiro Souma^a, Akio Murai*^a,b
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan
Fax: +81(11)7062714; e-Mail: fjwkn@sci.hokudai.ac.jp;
Present address: 6-14-44 Asabu-cho, Kita-ku, Sapporo 001-0045, Japan
Fax: +81(11)7476963; e-Mail: amurai@rmail.plala.or.jp;

Abstract

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Abstract

Chiral medium-sized monocyclic ethers corresponding to the D-, E-, F-, and I-ring parts of ciguatoxin have been synthesized from tri-O-acetyl-d-glucal through a common synthetic route involving ring-closing olefin metathesis.

Key words

Heterocycles - stereoselective synthesis - natural products - ethers - metathesis

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References

For isolation and structure determination of ciguatoxin, see:

1a Scheuer PJ. Takahashi W. Tsutsumi J. Yoshida T. Science 1967, 155: 1267

1b Tachibana K. Ph.D. Thesis University of Hawaii; Hawai: 1980.

1c Nukina M. Koyanagi LM. Scheuer PJ. Toxicon 1984, 22: 169

1d Murata M. Legrand A.-M. Ishibashi Y. Fukui M. Yasumoto T. J. Am. Chem. Soc. 1989, 111: 8929

1e Murata M. Legrand A.-M. Ishibashi Y. Fukui M. Yasumoto T. J. Am. Chem. Soc. 1990, 112: 4380

1f Satake M. Morohashi A. Oguri H. Oishi T. Hirama M. Harada N. Yasumoto T. J. Am. Chem. Soc. 1997, 119: 11325

1g For reviews on ciguatoxin and related marine toxins, see: Yasumoto T. Murata M. Chem. Rev. 1993, 93: 1897

1h See also: Scheuer PJ. Tetrahedron 1994, 50: 3

1i For a review on ciguatera, see: Lewis RL. Toxicon 2001, 39: 97

For the bioactivities of ciguatoxin and related compounds, see:

2a Bidard J.-N. Vijverberg HPM. Frelin C. Chungue E. Legrand A.-M. Bagnis R. Lazdanski M. J. Biol. Chem. 1984, 259: 8353

2b Lombet A. Bidard JN. Lazdanski M. FEBS Lett. 1987, 219: 355

2c For a review, see: Dechraoui M.-Y. Naar J. Pauillac S. Legrand A.-M. Toxicon 1999, 37: 125 ; see also the references cited in ref.1i

3 For the total synthesis of CTX3C, a congener of ciguatoxin, see: Hirama M. Oishi T. Uehara H. Inoue M. Maruyama M. Oguri H. Satake M. Science 2001, 294: 1904

For recent synthetic studies on ciguatoxins, see:

4a Sasaki M. Noguchi T. Tachibana K. J. Org. Chem. 2002, 67: 3301

4b Takai S. Isobe M. Org. Lett. 2002, 4: 1183

4c Bond S. Perlmutter P. Tetrahedron 2002, 58: 1779

4d Maruyama M. Inoue M. Oishi T. Oguri H. Ogasawara Y. Shindo Y. Hirama M. Tetrahedron 2002, 58: 1835

4e Kira K. Hamajima A. Isobe M. Tetrahedron 2002, 58: 1875

4f Sasaki M. Ishikawa M. Fuwa H. Tachibana K. Tetrahedron 2002, 58: 1889

4g Candenas ML. Pinto FM. Cintado CG. Morales EQ. Brouard I. Díaz MT. Rico M. Rodríguez E. Rodríguez RM. Pérez R. Pérez RL. Martín JD. Tetrahedron 2002, 58: 1921

4h Takakura H. Noguchi K. Sasaki M. Tachibana K. Angew. Chem. Int. Ed. 2001, 40: 1090

4i Oishi T. Tanaka S.-I. Ogasawara Y. Maeda K. Oguri H. Hirama M. Synlett 2001, 952

4j Imai H. Uehara H. Inoue M. Oguri H. Oishi T. Hirama M. Tetrahedron Lett. 2001, 42: 6219

4k Saeeng R. Isobe M. Heterocycles 2001, 54: 789

4l Oguri H. Tanaka S. Oishi T. Hirama M. Tetrahedron Lett. 2000, 41: 975

4m Sasaki M. Noguchi K. Fuwa H. Tachibana K. Tetrahedron Lett. 2000, 41: 1425

4n Kira K. Isobe M. Tetrahedron Lett. 2000, 41: 5951

4o Liu T.-Z. Isobe M. Tetrahedron 2000, 56: 5391

4p Liu T.-Z. Isobe M. Tetrahedron 2000, 56: 10209

4q Hosokawa S. Isobe M. J. Org. Chem. 1999, 64: 37

4r Leeuwenburgh MA. Kulker C. Overkleeft HS. van der Marel GA. van Boom JH. Synlett 1999, 1945

4s Oishi T. Nagumo Y. Shoji M. Le Brazidec J.-Y. Uehara H. Hirama M. Chem. Commun. 1999, 2035

4t Oishi T. Maruyama M. Shoji M. Maeda K. Kumahara N. Tanaka S. Hirama M. Tetrahedron 1999, 55: 7471

4u Oguri H. Sasaki S. Oishi T. Hirama M. Tetrahedron Lett. 1999, 40: 5405

4v Eriksson L. Guy S. Perlmutter P. Lewis R. J. Org. Chem. 1999, 64: 8396

4w Sasaki M. Inoue M. Takamatsu K. Tachibana K. J. Org. Chem. 1999, 64: 9399

4x Inoue M. Sasaki M. Tachibana K. J. Org. Chem. 1999, 64: 9416

4y Inoue M. Sasaki M. Tachibana K. Tetrahedron 1999, 55: 10949

For synthetic studies on ciguatoxin in this laboratory, see:

5a Oka T. Murai A. Chem. Lett. 1994, 1611

5b Oka T. Fujiwara K. Murai A. Tetrahedron 1996, 52: 12091

5c Atsuta H. Fujiwara K. Murai A. Synlett 1997, 307

5d Oka T. Fujiwara K. Murai A. Tetrahedron Lett. 1997, 38: 8053

5e Oka T. Murai A. Tetrahedron 1998, 54: 1

5f Oka T. Fujiwara K. Murai A. Tetrahedron 1998, 54: 21

5g Fujiwara K. Saka K. Takaoka D. Murai A. Synlett 1999, 1037

5h Fujiwara K. Tanaka H. Murai A. Chem. Lett. 2000, 610

5i Fujiwara K. Takaoka D. Kusumi K. Kawai K. Murai A. Synlett 2001, 691

For recent reviews on olefin metathesis, see:

6a Grubbs RH. Miller SJ. Fu GC. Acc. Chem. Res. 1995, 28: 446

6b Schuster M. Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36: 2067

6c Grubbs RH. Chang S. Tetrahedron 1998, 54: 4413

6d Armstrong SK. J. Chem. Soc., Perkin Trans. 1 1998, 371

6e Blechert S. Pure Appl. Chem. 1999, 71: 1393

6f Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3013

For the construction of an 8-membered cyclic trisubstituted alkene by the RCM reaction using Grubbs’ second generation catalyst 48,²¹ see:

7a Fürstner A. Thiel OR. Ackermann L. Schanz H.-J. Nolan SP. J. Org. Chem. 2000, 65: 2204

7b See also: Fürstner A. Thiel OR. Ackermann L. Org. Lett. 2001, 3: 449

8The similar ring cleavage of a C-glycoside for the preparation of a RCM precursor having a chiral dialkyl ether part has been applied for the total synthesis of prelaureatin in this laboratory:

8 Fujiwara K. Souma S. Mishima H. Murai A. Synlett 2002, 1493

9 Tulshian DB. Fraser-Reid B. J. Org. Chem. 1984, 49: 518

10 Cyanation of 8 was performed by the modified method of the following report: De Las Heras FG. San Felix A. Fernández-Resa P. Tetrahedron 1983, 39: 1617

11 Stereochemistry of the allylic hydroxy group in 14 or the homoallylic one in 16 was confirmed by ¹H NMR using modified Mosher’s method. See: Ohtani I. Kusumi T. Kashman Y. Kakisawa H. J. Am. Chem. Soc. 1991, 113: 4092

12 Hoffmann RW. Endesfelder A. Zeiß H.-J. Carbohydr. Res. 1983, 123: 320

13 Ferrier RJ. Methods Carbohydr. Chem. 1972, 6: 419

14 Evans DA. Polniaszek RP. Tetrahedron Lett. 1986, 27: 5683

15 Fu GC. Nguyen ST. Grubbs RH. J. Am. Chem. Soc. 1993, 115: 9856

16

Representative data for 2: a colorless oil; [α]_D ²² +23.3 (c, 0.06, CHCl₃); ¹H NMR (300 MHz, CDCl₃), δ 7.48 (2 H, m, Ph), 7.36 (3 H, m, Ph), 5.77 (2 H, m, H4, H5), 5.30 (1 H, s, acetal), 4.53 (1 H, dd, J = 12, 4.3 Hz, H8a), 4.31-4.17 (4 H, m, H1eq, H3, H6, H8b), 3.64 (1 H, t, J = 10 Hz, H1ax), 3.60-3.56 (1 H, m, H7), 3.52 (1 H, dt, J = 10, 4.8 Hz, H2), 2.92 (1 H, d, J = 5.7 Hz, 6-OH), 1.24 (9 H, s, t-Bu); IR (film): 3487, 2971, 2860, 1729, 1481, 1456, 1399, 1287, 1167, 1115, 1032, 977, 752, 698 cm^-1; HR-EIMS, calcd for C₂₀H₂₆O₆ (M)⁺: 362.1729, found: 362.1722.

17a Omura K. Swern D. Tetrahedron 1978, 34: 1651

17b Mancuso AJ. Huang S.-L. Swern D. J. Org. Chem. 1978, 43: 2480

17c Mancuso AJ. Swern D. Synthesis 1981, 165

18a Shimizu T. Hiranuma S. Nakata T. Tetrahedron Lett. 1996, 37: 6145

18b Shimizu T. Ohzeki T. Hiramoto K. Hori N. Nakata T. Synthesis 1999, 1373

19

Representative data for 3: a colorless oil; [α]_D ²¹ -9.2 (c 0.29, CHCl₃); ¹H NMR (400 MHz, CDCl₃, 55 °C), δ 7.28-7.48 (5 H, m, Ph), 5.74-5.82 (2 H, m, H5, H6), 5.40 (1 H, s, acetal), 4.52 (1 H, dd, J = 4.3, 10.3 Hz, H1eq), 3.77 (1 H, dd, J = 1.8, 10.6 Hz, H10a), 3.62-3.70 (2 H, m, H3, H8), 3.57 (1 H, dt, J = 4.3, 10.3 Hz, H2), 3.50 (1 H, t, J = 10.3 Hz, H1ax), 3.44 (1 H, dd, J = 7.7, 10.6 Hz, H10b), 3.32 (1 H, dt, J = 1.8, 7.7 Hz, H9), 2.68-2.80 (1 H, m, H4a), 2.44-2.58 (2 H, m, H7a, H4b), 2.28-2.43 (1 H, m, H7b), 0.91 (9 H, s, TBS), 0.90 (9 H, s, TBS), 0.098 (3 H, s, TBS), 0.070 (3 H, s, TBS), 0.066 (3 H, s, TBS), 0.049 (3 H, s, TBS); IR(film): 2955, 2928, 2856, 1471, 1462, 1389, 1361, 1294, 1258, 1213, 1148, 1103, 1027, 977, 836, 811, 776, 747, 665 cm^-1; HR-FDMS, calcd for C₂₉H₅₁O₅Si₂ (M + H)⁺: 535.3298, found: 535.3275.

20a Tebbe FN. Parshall GW. Reddy GS. J. Am. Chem. Soc. 1978, 100: 3611

20b Tebbe FN. Parshall GW. Reddy GS. J. Am. Chem. Soc. 1979, 101: 5074

20c Pine SH. Zahler R. Evans DA. Grubbs RH. J. Am. Chem. Soc. 1980, 102: 3270

20d Pine SH. Kim G. Lee V. Org. Synth. 1990, 69: 72

21 Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett. 1999, 1: 953

22a Crabtree RH. Felkin H. Morris GE. J. Chem. Soc., Chem. Commun. 1976, 716

22b Crabtree RH. Felkin H. Fellebeen-Khan T. Morris GE. J. Organometal. Chem. 1979, 168: 183

22c Crabtree RH. Davis MW. Organometallics 1983, 2: 681

22d Stork G. Kahne DE. J. Am. Chem. Soc. 1983, 105: 1072

23

Representative data for 4: a colorless oil; [α]_D ²⁵ +13.3 (c 0.15, CHCl₃); ¹H NMR [400 MHz, C₆D₆-CDCl₃ (1:1)], δ 7.66-7.72 (4 H, m, Ph), 7.51-7.47 (2 H, m, Ph), 7.33-7.15 (9 H, m, Ph), 5.29 (1 H, s, acetal), 4.08-4.17 (1 H, m, H1eq), 3.75 (1 H, dd, J = 10.5, 5.4 Hz, H9a), 3.69 (1 H, dd, J = 10.5, 5.9 Hz, H9b), 3.50-3.59 (1 H, m, H7), 3.42-3.50 (1 H, m, H3), 3.35-3.41 (2 H, m, H1ax, H2), 3.26 (1 H, brdt, J = 8.9, 5.5 Hz, H8), 2.28 (1 H, m, 7-OH), 1.91 (1 H, brdd, J = 13.8, 3.5 Hz, H4a), 1.62-1.64 (1 H, m, H5), 1.53-1.62 (3 H, m, H4b, H6), 1.09 (9 H, s, t-Bu), 1.00 (3 H, d, J = 7.1 Hz, 5-Me); IR(film): 3490, 3071, 3047, 2928, 2857, 1589, 1455, 1428, 1391, 1372, 1292, 1215, 1112, 1029, 916, 823, 744, 701, 615 cm^-1; HR-EIMS, calcd for C₂₉H₃₃O₅Si (M - t-Bu)⁺: 489.2097, found: 489.2105.