European Journal of Chemistry 2012, 3(3), 337-339. doi:10.5155/eurjchem.3.3.337-339.609

A simple formal stereoselective synthesis of Herbarumin III


Nagendra Siddavatam (1) , Krishnaiah Martha (2) , Krishna Reddy Vanka (3) , Biswanath Das (4,*)

(1) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500007, India
(2) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500007, India
(3) Department of Chemistry, Sri Krishnadevaraya University, Anantapur, 515055, India
(4) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500007, India
(*) Corresponding Author

Received: 16 Mar 2012, Accepted: 12 Apr 2012, Published: 30 Sep 2012

Abstract


A formal stereoselective synthesis of Herbarumin III has been accomplished starting from butanal involving Maruoka asymmetric allylation, diastereoselective iodine-induced electrophilic cyclization and conversion of iodocarbonate into syn-epoxy alcohol as the key steps.

3_3_337_339_800


Keywords


Nonenolide; Phytotoxic effect; Syn-epoxy alcohol; Maruoka allylation; Trimethylsulfonium iodide; Diastereoselective iodine-induced electrophilic cyclization

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DOI: 10.5155/eurjchem.3.3.337-339.609

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Citations

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[1]. Rathod Aravind Kumar, Jajula Kashanna, Paramesh Jangili, Biswanath Das
A simple stereoselective synthesis of (+)-[6]-gingerdiol
European Journal of Chemistry  4(3), 191, 2013
DOI: 10.5155/eurjchem.4.3.191-194.768
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[2]. Shaoxiang Yang, Wei Gong, Baoguo Sun, Yongguo Liu, Hongyu Tian
Synthesis of a New Odourant, 2-Mercapto-4-Heptanol
Journal of Chemical Research  39(3), 184, 2015
DOI: 10.3184/174751915X14253193792383
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References

[1]. Rivero-Cruz, J. F.; Cerda-Garcia-Rojas, C. M.; Mata, R. J. Nat. Prod. 2003, 66, 511-514.
http://dx.doi.org/10.1021/np020501t
PMid:12713403

[2]. Gurjar, M. K.; Karmakar, S.; Mahapatra, D. K. Tetrahedron Lett. 2004, 45, 4525-4526.
http://dx.doi.org/10.1016/j.tetlet.2004.04.040

[3]. Gurjar, M. K.; Nagaprasad, R.; Ramana, C. V.; Mahapatra, D. K. Arkivoc 2005, 3, 237-257.

[4]. Nanda, S. Tetrahedron Lett. 2005, 46, 3661-3663.
http://dx.doi.org/10.1016/j.tetlet.2005.03.139

[5]. Boruwa, J.; Bogoi, N.; Barua, N. C. Org. Biomol. Chem. 2006, 4, 3521-3525.
http://dx.doi.org/10.1039/b605982a

[6]. Gupta, P.; Kumar, P. Tetrahedron: Asymmetr. 2007, 18, 1688-1692.
http://dx.doi.org/10.1016/j.tetasy.2007.07.022

[7]. Chen, X. S.; Da, S. J.; Yang, L. H.; Xu, B. Y.; Xie, Z. X.; Li, Y. Chin. Chem. Lett. 2007, 18, 255-257.
http://dx.doi.org/10.1016/j.cclet.2007.01.035

[8]. Yadav, J. S.; Atter, H.; Gayathri, K. U.; Rao, N. V.; Prasad, A. R. Synthesis 2008, 3945-3950.
http://dx.doi.org/10.1055/s-0028-1083249

[9]. Sabitha, G.; Srinivas, C.; Maruthi, C.; Yadav, J. S. Helv. Chim. Acta. 2010, 93, 1634-1640.
http://dx.doi.org/10.1002/hlca.200900427

[10]. Das, B.; Suneel, K.; Satyalaxmi, G.; Kumar, D. N. Tetrahedron: Asymmetr. 2009, 20, 1536-1540.
http://dx.doi.org/10.1016/j.tetasy.2009.05.036

[11]. Das, B.; Krishnaiah, M.; Sudhakar, C. Bioorg. Med. Chem. Lett. 2010, 20, 2303-2305.
http://dx.doi.org/10.1016/j.bmcl.2010.01.162

[12]. Das, B.; Kumar, D. N. Synlett 2011, 1285-1287.
http://dx.doi.org/10.1055/s-0030-1260546

[13]. Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
http://dx.doi.org/10.1021/ja020338o
PMid:12580590

[14]. Bartlett, P. A.; Meadows, J. D.; Brown. E. G.; Morimoto, A.; Jernstedt, K. K. J. Org. Chem. 1982, 47, 4013-4018.
http://dx.doi.org/10.1021/jo00142a002

[15]. Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626-4633.
http://dx.doi.org/10.1021/jo00145a004


How to cite


Siddavatam, N.; Martha, K.; Vanka, K.; Das, B. Eur. J. Chem. 2012, 3(3), 337-339. doi:10.5155/eurjchem.3.3.337-339.609
Siddavatam, N.; Martha, K.; Vanka, K.; Das, B. A simple formal stereoselective synthesis of Herbarumin III. Eur. J. Chem. 2012, 3(3), 337-339. doi:10.5155/eurjchem.3.3.337-339.609
Siddavatam, N., Martha, K., Vanka, K., & Das, B. (2012). A simple formal stereoselective synthesis of Herbarumin III. European Journal of Chemistry, 3(3), 337-339. doi:10.5155/eurjchem.3.3.337-339.609
Siddavatam, Nagendra, Krishnaiah Martha, Krishna Reddy Vanka, & Biswanath Das. "A simple formal stereoselective synthesis of Herbarumin III." European Journal of Chemistry [Online], 3.3 (2012): 337-339. Web. 17 Sep. 2019
Siddavatam, Nagendra, Martha, Krishnaiah, Vanka, Krishna, AND Das, Biswanath. "A simple formal stereoselective synthesis of Herbarumin III" European Journal of Chemistry [Online], Volume 3 Number 3 (30 September 2012)

DOI Link: https://doi.org/10.5155/eurjchem.3.3.337-339.609

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