E. Bourcet et al. / Tetrahedron Letters 50 (2009) 1787–1790
1789
1.2%
Supplementary data
CH3
0.7%
O
H7
O
H3e
O
O
References and notes
1.
(a) Sone, H.; Kigoshi, H.; Yamada, K. J. Org. Chem. 1996, 61, 8956–8960; b
Kornprobst, J.-M. In Substances naturelles d’origine marine, Tec&Doc ed., Paris,
Figure 2. NOE experiments on compound 10a.
2005, pp 1313–1315.
2.
(a) Pettit, G. R.; Xu, J.-P.; Doubek, D. L.; Chapuis, J.-L.; Schmidt, J. M. J. Nat. Prod.
2
2
004, 67, 1252–1255; (b) Paterson, I.; Findlay, A. D.; Florence, G. J. Org. Lett.
006, 8, 2131–2134.
7
OTBS
7
OTBS
3
4
5
.
.
.
Sone, H.; Suenaga, K.; Bessho, Y.; Kondo, T.; Kigoshi, H.; Yamada, K. Chem. Lett.
1998, 85–86.
Paterson, I.; Florence, G. J.; Heimann, A. C.; Mackay, A. C. Angew. Chem., Int. Ed.
2005, 44, 1130–1133.
Suenaga, K.; Hoshino, H.; Yoshii, T.; Mori, K.; Sone, H.; Bessho, Y.; Sakakura, A.;
Hayakawa, I.; Yamada, K.; Kigoshi, H. Tetrahedron 2006, 62, 7687–7698.
O
O
HO
VO(acac)2
HO
3
3
t-BuOOH, 0°C
O
CH Cl , 4A MS
2
2
O
O
6. Tello-Aburto, R.; Olivo, H. F. Org. Lett. 2008, 10, 2191–2194. and references cited
therein.
7
.
(a) Inanaga, J.; Hirata, K.; Saeki, T.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc.
Jpn. 1979, 52, 1989–1993; (b) Parenty, A.; Moreau, X.; Campagne, J.-M. Chem.
Rev. 2006, 106, 911–939.
Hoye, T. R.; Danielson, M. E.; May, A. E.; Zhao, H. Angew. Chem., Int. Ed. 2008, 47,
9743–9746.
8
a
11 (90%)
OH
8
.
.
7
OTBS
9
Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413–4450.
Dess-Martin
periodinane
1.3 equiv.)
O
OTBS
1
0. (a) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371–388; (b) Connon, S.
J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900–1923; (c) Nicolaou, K. C.;
Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2006, 45, 4490–4527; (d) Clavier,
H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S. P. Angew. Chem., Int. Ed.
2007, 46, 6786–6801.
(
PhSe)2
3
O
O
7
(
3
NaBH4
EtOH, 0°C
O
O
O
CH Cl , rt
2
2
1
1. RCM and formation of 14-membered ring lactones: (a) Goldring, W. P. D.;
Hodder, A. S.; Weiler, L. Tetrahedron Lett. 1998, 39, 4955–4958; (b) Lee, C. W.;
Grubbs, R. H. Org. Lett. 2000, 2, 2145–2147; (c) Fürstner, A.; Thiel, O. R.;
Ackermann, L. Org. Lett. 2001, 3, 449–451; (d) Fürstner, A.; Ackermann, L.;
Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.
Eur. J. 2001, 7, 3236–3253; (e) Ronsheim, M. D.; Zercher, C. K. J. Org. Chem.
O
1
2 (68%)
13 (87%)
2003, 68, 1878–1885; (f) Hanessian, S.; Giroux, S.; Buffat, M. Org. Lett. 2005, 7,
3889–3992; (g) Krauss, J.; Bracher, F.; Unterreitmeier, D. Arch. Pharm. Chem.
2006, 339, 629–632; (h) Conrad, J. C.; Eelman, M. D.; Duarte Silva, J. A.;
OH
5
Monfette, S.; Parnas, H. H.; Snelgrove, J. L.; Fogg, D. E. J. Am. Chem. Soc. 2007,
129, 1024–1025; (i) Schulz, S.; Yildizhan, S.; Stritzke, K.; Estrada, C.; Gilbert, L.
H. Org. Biomol. Chem. 2007, 3434–3447; (j) Vougioukalakis, G. C.; Grubbs, R. H.
J. Am. Chem. Soc. 2008, 130, 2234–2245; (k) Xuan, R.; Oh, H.-S.; Lee, Y.; Kang,
H.-Y. J. Org. Chem. 2008, 73, 1456–1461.
3
7
O
OH
OMe
O
O
1
1
2. (a) Ipaktschi, J.; Sang, B. Liebigs Ann. Chem. 1992, 1029–1032; (b) Bott, S. G.;
Marchand, A. P.; Kumar, K. A. J. Chem. Crystallogr. 1996, 26, 429–433; (c) Mohr,
P. C.; Rademacher, P. Synthesis 2008, 188–190.
3. (a) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130–9136; (b) Ley,
S. V.; Cleator, E.; Harter, J.; Hollowood, C. J. Org. Biomol. Chem. 2003, 3263–
3264; (c) Fawcett, J.; Griffiths, G. A.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer,
N. S.; Uneyama, E. Chem. Commun. 2004, 302–303; (d) Miles, J. A. L.; Mitchell,
L.; Percy, J. M.; Singh, K.; Uneyama, E. J. Org. Chem. 2007, 72, 1575–1587.
4. (a) White, J. D.; Hrnviar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359–
OH
CSA
3
(
0.05 equiv.)
O
7
14 (42%)
+
14' (42%)
OH
MeOH, rt
O
O
5
3
7
1
O
7360; (b) Maier, M. E.; Lapeva, T. Synlett 1998, 891–893; (c) White, J. D.;
OMe
O
Hrnciar, P. J. Org. Chem. 2000, 65, 9129–9142; (d) Layton, M. E.; Morales, C. A.;
Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773–775; (e) Bieräugel, H.; Jansen, T. P.;
Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673–
O
2674; (f) Dalgard, J. E.; Rychnovsky, S. D. Org. Lett. 2004, 6, 2713–2716; (g)
Petri, A. F.; Bayer, A.; Maier, M. E. Angew. Chem., Int. Ed. 2004, 43, 5821–5823;
(h) Wang, X.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2005, 44, 3067–3071; (i)
Redon, S.; Piva, O. Tetrahedron Lett. 2006, 47, 733–736; (j) Lauritsen, A.;
Madsen, R. Org. Biomol. Chem. 2006, 4, 2898–2905; (k) Jung, Y.-H.; Kim, Y.-J.;
Lee, J.; Tae, J. Chem. Asian J. 2007, 2, 656–661; (l) Balskus, E. P.; Jacobsen, E. N.
Science 2007, 317, 1736–1740; (m) Anzo, T.; Suzuki, A.; Sawamura, K.;
Motozaki, T.; Hatta, M.; Takao, K.-i.; Tadano, K.-i. Tetrahedron Lett. 2007, 48,
8442–8448; (n) Fürstner, A.; Korte, A. Chem. Asian J. 2008, 3, 310–318; (o) Craft,
D. T.; Gung, B. W. Tetrahedron Lett. 2008, 49, 5931–5934; (p) Farran, D.; Parrot,
I.; Toupet, L.; Martinez, J.; Dewynter, G. Org. Biomol. Chem. 2008, 6, 3989–3996.
5. (a) Zibuck, R.; Streiber, J. J. Org. Chem. 1989, 54, 4717–4719; (b) Zibuck, R.;
Streiber, J. Org. Synth. 1993, 71, 236–242; (c) Dewi-Wülfing, P.; Gebauer, J.;
Blechert, S. Synlett 2006, 487–489.
0
Scheme 4. Synthesis of 5-hydroxymacrolactones 14 and 14 .
tone 10a. Further investigations performed also on the acetate de-
0
rived from 14 confirm this attribution.
In conclusion, we have developed a short access to the core
structure of aurisides and related marine macrolides. Work is
now in progress to apply this strategy to the total synthesis of auri-
side A and will be reported in due course.
1
1
6. (a) Tanaka, S.; Yamamoto, H.; Nozaki, H.; Sharpless, K. B.; Michaelson, R. C.;
Cutting, J. D. J. Am. Chem. Soc. 1974, 96, 5254; (b) Hoveyda, A. H.; Evans, D.; Fu,
G. Chem. Rev. 1993, 93, 1307–1370; (c) Adam, W.; Beck, A. K.; Pichota, A.; Saha-
Möller, C. R.; Seebach, D.; Vogl, N.; Zhang, R. Tetrahedron: Asymmetry 2003, 14,
Acknowledgments
1355–1361.
1
7. (a) Lauret, C. Tetrahedron: Asymmetry 2001, 12, 2359–2383; (b) Takano, S.;
Moriya, M.; Ogasawara, K. Synlett 1993, 601–602; (c) Desmaële, D.; d’Angelo, J.
J. Org. Chem. 1994, 59, 2292–2303; (d) Tosaki, S.-y.; Horiuchi, Y.; Nemoto, T.;
Ohshima, T.; Shibasaki, M. Chem. Eur. J. 2004, 10, 1527–1544; (e) Hanessian, S.;
Mainetti, E.; Lecomte, F. Org. Lett. 2006, 8, 4047–4049.
E.B. thanks the ‘Ministère de l’Education Nationale, de la
Recherche et de la Technologie’ for a doctoral fellowship. This work
was partly supported by European Union FP6 Integrated Project
No. 503467 on protein kinases.