메뉴 건너뛰기




Volumn 55, Issue 3, 2007, Pages 495-499

Synthetic study on telomerase inhibitor, D8646-2-6: Synthesis of the key intermediate using Sn(OTf)2 or Sc(OTf)3 mediated aldol-type reaction and stille coupling

Author keywords

Aldol type reaction; Carbohydrate containing pyrone; Scandium triflate; Stille coupling; Tin triflate; Vinyl stannane which contains phosphonate

Indexed keywords

ALDEHYDE; C 3 PYRANOSYL 4 HYDROXY 2 PYRONE DERIVATIVE; D8646 2 6; PYRONE DERIVATIVE; SCANDIUM; TELOMERASE INHIBITOR; TIN; UNCLASSIFIED DRUG;

EID: 34047171283     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.495     Document Type: Article
Times cited : (8)

References (35)
  • 2
    • 21244491657 scopus 로고    scopus 로고
    • Review of natural products containing pyrone ring, see
    • Review of natural products containing pyrone ring, see: McGlacken G. P., Fairlamb Ian J. S., Nat. Prod. Rep., 22, 369-385 (2005).
    • (2005) Nat. Prod. Rep , vol.22 , pp. 369-385
    • McGlacken, G.P.1    Fairlamb Ian, J.S.2
  • 3
    • 22444433706 scopus 로고    scopus 로고
    • Recent report for natural products containing conjugated polyene see
    • Recent report for natural products containing conjugated polyene see: Wang F., Luo D.-Q., Liu J.-K., J. Antibiot., 58, 412-415 (2005).
    • (2005) J. Antibiot , vol.58 , pp. 412-415
    • Wang, F.1    Luo, D.-Q.2    Liu, J.-K.3
  • 5
    • 0347022270 scopus 로고    scopus 로고
    • Recent report for natural products containing conjugated polyene see
    • Recent report for natural products containing conjugated polyene see: Weber R. W. S., Muci A., Davoli P., Tetrahedron Lett., 45, 1075-1078 (2004).
    • (2004) Tetrahedron Lett , vol.45 , pp. 1075-1078
    • Weber, R.W.S.1    Muci, A.2    Davoli, P.3
  • 6
    • 31944434238 scopus 로고    scopus 로고
    • Review for natural products containing polyene, see
    • Review for natural products containing polyene, see: Ishibashi M., Med. Chem., 1, 575-590 (2005).
    • (2005) Med. Chem , vol.1 , pp. 575-590
    • Ishibashi, M.1
  • 7
    • 0036009991 scopus 로고    scopus 로고
    • Review for natural products containing polyene, see
    • Review for natural products containing polyene, see: Thirsk C., Whiting A., J. Chem. Soc., Perkin Trans. 1, 2002, 999-1023 (2002).
    • (2002) J. Chem. Soc., Perkin Trans. 1 , vol.2002 , pp. 999-1023
    • Thirsk, C.1    Whiting, A.2
  • 10
    • 34047173392 scopus 로고    scopus 로고
    • Scott W. J., The Stille Reaction in Organic Reactions, 50, Chap. 1, ed. by Paquette L. A., John Willey & Sons, Inc., New York, 1997, pp. 1-652.
    • Scott W. J., "The Stille Reaction in Organic Reactions," Vol. 50, Chap. 1, ed. by Paquette L. A., John Willey & Sons, Inc., New York, 1997, pp. 1-652.
  • 12
    • 27944498961 scopus 로고    scopus 로고
    • For the aldol reaction of pyrone, see
    • For the aldol reaction of pyrone, see: Kirsch S. F., Bach T., Chem. Eur. J., 11, 7007-7023 (2005).
    • (2005) Chem. Eur. J , vol.11 , pp. 7007-7023
    • Kirsch, S.F.1    Bach, T.2
  • 13
    • 0033690703 scopus 로고
    • For the aldol reaction of pyrone, see:, and references therein. 2000
    • For the aldol reaction of pyrone, see: Casiraghi G., Zanardi F., Appendino G., Rassu G., Chem. Rev., 100, 1929-1972 (2000), and references therein.
    • (1929) Chem. Rev , vol.100
    • Casiraghi, G.1    Zanardi, F.2    Appendino, G.3    Rassu, G.4
  • 15
    • 0029046854 scopus 로고
    • For the aldol reaction of pyrone, see
    • For the aldol reaction of pyrone, see: Lyga J. W., J. Heterocyclic Chem., 32, 515-518 (1995).
    • (1995) J. Heterocyclic Chem , vol.32 , pp. 515-518
    • Lyga, J.W.1
  • 16
    • 0028109279 scopus 로고
    • For the aldol reaction of pyrone, see
    • For the aldol reaction of pyrone, see: Paterson I., Wallace D. J., Tetrahedron Lett., 35, 9477-9480 (1994).
    • (1994) Tetrahedron Lett , vol.35 , pp. 9477-9480
    • Paterson, I.1    Wallace, D.J.2
  • 17
    • 0344580699 scopus 로고
    • For the aldol reaction of pyrone, see
    • For the aldol reaction of pyrone, see: Munchhof M. J., Heathcock C. H., J. Org. Chem., 59, 7566-7567 (1994).
    • (1994) J. Org. Chem , vol.59 , pp. 7566-7567
    • Munchhof, M.J.1    Heathcock, C.H.2
  • 18
    • 0000499691 scopus 로고
    • For the aldol reaction of pyrone, see
    • For the aldol reaction of pyrone, see: Suh H., Wilcox C. S., J. Am. Chem. Soc., 110, 470-481 (1988).
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 470-481
    • Suh, H.1    Wilcox, C.S.2
  • 20
    • 0001360042 scopus 로고
    • For the aldol reaction of pyrone, see
    • For the aldol reaction of pyrone, see: Williams D. R., White F. H., J. Org. Chem., 52, 5067-5079 (1987).
    • (1987) J. Org. Chem , vol.52 , pp. 5067-5079
    • Williams, D.R.1    White, F.H.2
  • 21
    • 0142014422 scopus 로고
    • For the aldol reaction of pyrone, see
    • For the aldol reaction of pyrone, see: Wachter M. P., Harris T. M., Tetrahedron, 26, 1685-1694 (1970).
    • (1970) Tetrahedron , vol.26 , pp. 1685-1694
    • Wachter, M.P.1    Harris, T.M.2
  • 23
    • 0024375471 scopus 로고
    • For the alkylation of pyrone, see
    • For the alkylation of pyrone, see: Jones R. C. F., Patience J. M., Tetrahedron Lett., 30, 3217-3218 (1989).
    • (1989) Tetrahedron Lett , vol.30 , pp. 3217-3218
    • Jones, R.C.F.1    Patience, J.M.2
  • 25
    • 34047132597 scopus 로고    scopus 로고
    • Since all protective groups are desirable to be deprotected in one operation at the final step, benzyl group was chosen as the protective group
    • Since all protective groups are desirable to be deprotected in one operation at the final step, benzyl group was chosen as the protective group.
  • 26
    • 34047181900 scopus 로고    scopus 로고
    • Direct C-glycosylation of 4-benzyloxy-6-methyl pyrone gave only α-C-glycoside in low yield.
    • Direct C-glycosylation of 4-benzyloxy-6-methyl pyrone gave only α-C-glycoside in low yield.
  • 27
    • 34047121085 scopus 로고    scopus 로고
    • Protection of the hydroxyl group of pyrone moiety proceeded smoothly to afford the corresponding benzyl ether 7 in 86% yield as a mixture of rotamers under Mitsunobu conditions (DEAD, PPh3 and BnOH).The 1H-NMR (CDCl3 at 25 °C) of benzyl protected pyrone 7 was rather complex, and it seemed to be a mixture of two isomers. However, the 1H-NMR of 7 in DMSO-d6 at 80 °C was gathered and bundled to single isomer. That means that C 3-β-galactopyranosyl-4-benzyloxy-6-methylpyrone might exist as a mixture of rotamer at 25 °C. In contrast, a rotamer was not observed in the case of the corresponding α-isomer
    • 3-β-galactopyranosyl-4-benzyloxy-6-methylpyrone might exist as a mixture of rotamer at 25 °C. In contrast, a rotamer was not observed in the case of the corresponding α-isomer.
  • 29
    • 34047092652 scopus 로고    scopus 로고
    • The reaction was monitored by TLC analyses before it was quenched, alcohol 12 was major product, however after being quenched, triene 11 was major product. Alcohol 12 has corelation of terminal methyl proton and methine proton of carbon bearing hydroxyl group in the COSY spectrum.
    • The reaction was monitored by TLC analyses before it was quenched, alcohol 12 was major product, however after being quenched, triene 11 was major product. Alcohol 12 has corelation of terminal methyl proton and methine proton of carbon bearing hydroxyl group in the COSY spectrum.
  • 33
    • 34047178784 scopus 로고
    • Aldehyde 6 was prepared from pyridinium-1-sulfonate according to the literature, see: Becher J
    • Aldehyde 6 was prepared from pyridinium-1-sulfonate according to the literature, see: Becher J., Org. Synth., 59, 79-84 (1979).
    • (1979) Org. Synth , vol.59 , pp. 79-84
  • 34
    • 15444381139 scopus 로고    scopus 로고
    • Mukaiyama aldol-type reaction using aldehyde 6 was reported, see: Paterson I., Florence G. J., Heimann A. C., Mackay A. C., Angew. Chem. Int. Ed., 44, 1130-1133 (2005).
    • Mukaiyama aldol-type reaction using aldehyde 6 was reported, see: Paterson I., Florence G. J., Heimann A. C., Mackay A. C., Angew. Chem. Int. Ed., 44, 1130-1133 (2005).
  • 35
    • 34047130056 scopus 로고    scopus 로고
    • 3N gave the desired triene 15 only in 30% yield due to competitive retro aldol reaction.
    • 3N gave the desired triene 15 only in 30% yield due to competitive retro aldol reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.