G. Venkata Ramana, B. Venkateswara Rao / Tetrahedron Letters 44 (2003) 5103–5105
5105
Reductive elimination of 21 with activated Zn under
sonication conditions yielded olefinic aldehyde 22
(Scheme 2), which was further treated with vinylmagne-
sium bromide giving allyl alcohol 23. Finally (+)-penteno-
2. (a) Umino, K.; Furama, T.; Matzuzawa, N.; Awataguchi,
Y.; Ito, Y.; Okuda, T. J. Antibiot. 1973, 26, 506–512; (b)
Umino, K.; Takeda, N.; Ito, Y.; Okuda, T. Chem. Pharm.
Bull. 1974, 22, 1233–1238.
mycin
2 was synthesized via 26 (mp 63–65°C,
3. (a) Stephen, J. B.; Smith, A. B. J. Am. Chem. Soc. 1978, 100,
7767–7768; (b) Smith, A. B., III; Stephen, J. B.; Nancy, N.
P.; Micheal, A. G. J. Org. Chem. 1982, 47, 1855–1869; (c)
Verlaak, J. M. J.; Klunder, A. J. H.; Zwanenburg, B.
Tetrahedron Lett. 1982, 23, 5463–5466; (d) John, D. E.;
Michael, H.; Malcolm, N. P.; Neil, P.; Richard, J. S.
Tetrahedron Lett. 1983, 24, 965–968; (e) Michael, H.; Neil,
P.; Richard, J. S.; Malcolm, N. P. J. Chem. Soc., Perkin
Trans. 1 1984, 2089–2096; (f) Pohmakotr, M.; Popuang, S.
Tetrahedron Lett. 1991, 32, 275–278.
4. (a) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.;
Grant, B. D.; Fitch, W. L.; Moffatt, J. G. Pure. Appl. Chem.
1978, 50, 1363–1383; (b) Sugahara, T.; Ogasawava, K.
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[h]2D5=−21.16 (c 1.0, CHCl3)) using the conditions
described in Scheme 1 for (−)-pentenomycin 1. The
spectroscopic (1H and 13C) data for 2 were in agreement
with the (−)-isomer 1. [h]2D5=+30.1 (c 0.1, EtOH).
In summary, we have used a common strategy for the
synthesis of (−)- and (+)-pentenomycins9 using reductive
iodo elimination and RCM, starting from commercially
available
yields.
D-mannose and D-ribose respectively in good
Acknowledgements
G. V. Ramana thanks the CSIR, New Delhi for a research
fellowship (SRF). We also thank Dr. J. S. Yadav and Dr.
G. V. M. Sharma for their support and encouragement.
5. Carina, S. P.; Robert, M. J. Org. Chem. 2002, 67, 4441–4449
and references cited therein.
6. Pak-Tsun, Ho. Can. J. Chem. 1979, 57, 381–383.
7. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans.
1 1980, 2866–2869.
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