R. S. Ferrarini et al. / Tetrahedron Letters 51 (2010) 6843–6846
6845
PhMe2SiCl
1) Li0, THF, 0 ºC, 16 h
2) 0.5 eq CuCN
0 ºC, 20 min
O
OLi
R
O
H
[(PhMe2Si)2Cu(CN)Li2]
SiMe2Ph
H
SiMe2Ph
O
H3O+
O
γ
(12)
γ
O
H
Me
α
Me
β
α
β
-70 ºC
R
R
H
H
H+
R = nBu, (S)-5a
R = nHex, (S)-5b
R = nBu, 9a, 84%
R = nHex, 9b, 82%
Scheme 6. Diastereoselective 1,4-addition of 12 to (S)-5a and (S)-5b.
O
O
Woerpel, K. A. Org. Lett. 2001, 3, 675–678; (f) Nishiyama, T.; Nishioka, T.; Esumi,
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R
R
KBr / NaOAc / AcOOH
0 ºC, then 2h, r.t.
O
O
PhMe2Si
HO
R= nBu,
R= nHex,
R= nBu, , 93%
9a
9b
2
R= nHex, , 91%
4
Scheme 7. Fleming–Tamao oxidation of 9a and 9b.
O
O
R
R
routes A or B
O
O
O
HO
O
R = nBu, 2
R = nHex, 4
R= nBu, 1
R= nHex, 3
route A = iBuCOCl / DMAP / Et3N
1, 80%; 3, 84%
route B = iBuCOCl / py
1, 96%, > 97% ee; 3, 96%, > 97% ee
Scheme 8. Preparation of 1 and 3.
they are solvent free, they can be safely handled in the presence of
air and light.
In conclusion, the stereoselective synthesis of compounds 1, 2,
3, and 417 was accomplished in few steps, with good yields and
enantiomeric excesses, starting from Z-vinylic hydroxytellurides
6. In principle, the compounds with opposite configurations could
be prepared in a similar way making use of the same telluride 6 of
the R configuration, obtained by enzymatic kinetic resolution of
the racemic telluride 6. The versatility of our approach could allow
the preparation of a number of naturally occurring butenolides
with trans, trans relative stereochemistry in both enantiomerically
enriched forms.
4. Ugurchieva, T. M.; Veselovsky, V. V. Russ. Chem. Rev. 2009, 78, 337–373.
5. Bassora, B. K.; Costa, C. E.; Gariani, R. A.; Comasseto, J. V.; Dos Santos, A. A.
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1313; (b) Comasseto, J. V.; Barrientos-Astigarraga, R. E. Aldrichim. Acta 2000, 33,
66–78.
7. (a) Comasseto, J. V.; Gariani, R. A. Tetrahedron 2009, 65, 8447–8459; (b) Dos
Santos, A. A.; Da Costa, C. E.; Princival, J. L.; Comasseto, J. V. Tetrahedron:
Asymmetry 2006, 17, 2252–2259.
8. For recent reviews see: (a) Petragnani, N.; Stefani, H. A. Tellurium in Organic
Synthesis: Best Synthetic Methods, 2nd ed.; Academic Press: London, 2007; (b)
Comasseto, J. V.; Clososki, G. C.; Cunha, R. L. O. R. In Mingos, D. M. P., Crabtree,
R. H., Eds.; Tellurium in: Comprehensive Organometallic Chemistry III;
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Santos, A. A. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 939–947; (d)
Wendler, E. P.; Dos Santos, A. A. Synlett 2009, 7, 1034–1040.
9. For recent examples see: (a) Schneider, C. C.; Caldeira, H.; Gay, B. M.; Back, D. F.;
Zeni, G. Org. Lett. 2010, 12, 936–939; (b) Myrzayans, P. M.; Pouwer, R. H.;
Williams, C. M. Org. Lett. 2008, 10, 3861–3863; (c) Myrzayans, P. M.; Pouwer, R.
H.; Williams, C. M.; Bernhardt, P. V. Tetrahedron 2009, 65, 8297–8305.
10. (a) Fleming, I.; Reddy, N. L.; Takaki, K.; Ware, A. C. J. Chem. Soc., Chem. Commun.
1987, 1472–1474; (b) Harcken, C.; Rank, E.; Bruckner, R. Chem. Eur. J. 1998, 4,
2342–2352.
11. (a) Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229–4232; (b)
Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem.
Soc., Perkin Trans. 1 1995, 317–337.
Acknowledgments
The authors thank FAPESP, CAPES and CNPq for the financial
support. Amano Pharmaceutical Co. and Novozymes Inc. are
acknowledged for their generous gifts of lipases.
References and notes
1. (a) Yonehara, H.; Takeuchi, S. J. Antibiot., Ser. A 1958, 11, 254–263; (b) Kinoshita,
M.; Wada, M.; Umezawa, S. J. Antibiot. 1969, 22, 580–582; (c) Liu, W. C.; van
Tamelen, E. E.; Strong, F. M. J. Am. Chem. Soc. 1960, 82, 1652–1654.
2. Alali, F. Q.; Liu, X. X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504–540.
3. For enantioselective syntheses of compounds 1–4 see: (a) Chakraborty, T. K.;
Chattopapadhyay, A. K.; Ghosh, S. Tetrahedron Lett. 2007, 48, 1139–1142; (b)
Yang, Y.-Q.; Wu, Y.-K. Chin. J. Chem. 2005, 23, 1519–1522; (c) He, M.; Lei, A.;
Zhang, X. Tetrahedron Lett. 2005, 46, 1823–1826; (d) Krishna, P. R.; Ramana
Reddy, V. V.; Sharma, G. V. M. Synthesis 2004, 13, 2107–2114; (e) Peng, Z.-H.;
12. Ouchi, A.; Hyugano, T.; Liu, C. Org. Lett. 2009, 11, 4870–4876.
13. For (R)-5a and (S)-5a see: He, Y.-T.; Yang, H. N.; Yao, Z.-T. Tetrahedron 2002, 58,
8805–8810 (b) (S)-5b was derivatized to 9b and then the absolute
configuration was determined by comparing the optical rotation value of the
9b, with that described in Ref. 3j for the same compound..