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Synthesis 2014; 46(12): 1639-1647
DOI: 10.1055/s-0033-1341154
DOI: 10.1055/s-0033-1341154
paper
Iterative Iodocyclization: Total Synthesis of Polyrhacitide B
Authors
Further Information
Publication History
Received: 09 February 2014
Accepted after revision: 14 March 2014
Publication Date:
11 April 2014 (online)
Abstract
A highly stereoselective total synthesis of polyrhacitide B is reported. Key reactions are an iodocyclization protocol developed in our group, the Maruoka asymmetric allylation, the Bartlett–Smith iodocarbonate cyclization, and iodolactonization.
Key words
natural products - total synthesis - iodine-catalyzed cyclization - asymmetric allylation - iodocarbonate cyclization - oxidative cleavageSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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References and Notes
- 1 Puyvelds LV, Dube S, Uwimana E, Uwera C, Dommisse RA, Jiang ZH, Yang QX, Tanaka T, Kouno I. J. Nat. Prod. 2008; 71: 724
- 2a Zhang JH, Ma AH, Xie XF, Li SL. Jiangsu J. TCM 1996; 17: 43
- 2b Zhang RW, Shao SH. J. Jiangxi College TCM 1996; 8: 47
- 2c Li SL, Ren YJ, Cui X, Qian ZZ, Chin QD. Tradit. Pat. Med. 1994; 17: 47
- 3a Esmans EL, Schoor OV, Vlietinek AJ. Phytochemistry 1979; 18: 1215
- 3b Drewes SE, Horn MM, Schoor RS. Phytochemistry 1995; 40: 321
- 3c Drewes SE, Sehlapelo BM, Horn MM, Scott-Shaw RS, Sandor P. Phytochemistry 1995; 38: 1427
- 3d Drewes SE, Horn MM, Wijewardene CS. Phytochemistry 1996; 41: 333
- 3e Drewes SE, Horn MM, Mavi S. Phytochemistry 1997; 44: 437
- 3f Collett LA, Davies-Coleman MT, Rivett DE. A, Drewes SE, Horn MM. Phytochemistry 1997; 44: 935
- 3g Collett LA, Davies-Coleman MT, Rivett DE. A. Phytochemistry 1998; 48: 651
- 3h Takeda Y, Okada Y, Masuda T, Hirata E, Takushi A, Otsuka S. Phytochemistry 1998; 49: 2565
- 4 Rychnovsky SD, Rogers B, Yang G. J. Org. Chem. 1993; 58: 3511
- 5 Ohtani I, Kusumi J, Kashman Y, Kakisawa H. J. Am. Chem. Soc. 1991; 113: 4092
- 6 Yoshida WY, Bryan PJ, Baker BJ, McClintock JB. J. Org. Chem. 1995; 60: 780
- 7 Kou J, Ni Y, Li N, Wang J, Liu L, Jiang Z.-H. Biol. Pharm. Bull. 2005; 28: 176
- 8 Menz H, Kirsch SF. Org. Lett. 2009; 11: 5634
- 9a Yadav JS, Rajendar G, Ganganna B, Srihari P. Tetrahedron Lett. 2010; 51: 2154
- 9b Yadav JS, Rajendar G. Eur. J. Org. Chem. 2011; 6781
- 9c Ghosh S, Nageswara Rao Ch. Tetrahedron Lett. 2010; 51: 2052
- 10 Mohapatra DK, Das PP, Pattanayak MR, Yadav JS. Chem. Eur. J. 2010; 16: 2072
- 11 Mohapatra DK, Bhimireddy E, Krishnarao PS. R, Das PP, Yadav JS. Org. Lett. 2011; 13: 744
- 12a Marshall JA, Schaaf G, Nolting A. Org. Lett. 2005; 7: 5331
- 12b Nielsen LP. C, Stevenson CP, Blackmond DG, Jacobsen EN. J. Am. Chem. Soc. 2004; 126: 1360
- 13 Bieniek M, Bujok R, Cabaj M, Lugan N, Lavigne G, Arlt D, Grela K. J. Am. Chem. Soc. 2006; 128: 13652
- 14 Yu W, Mei Y, Hua Z, Jin Z. Org. Lett. 2004; 6: 3217
- 15 Hanawa H, Hashimoto T, Maruoka K. J. Am. Chem. Soc. 2003; 125: 1708
- 16 Moreau X, Bazan-Tejeda B, Campagne J.-M. J. Am. Chem. Soc. 2005; 127: 7288
- 17a Bartlett PA, Meadows JD, Brown EG, Morimoto A, Jernstedt KK. J. Org. Chem. 1982; 47: 4013
- 17b Duan JJ.-W, Smith AB. III. J. Org. Chem. 1993; 58: 3703
- 18 Crimmins MT, Slade DJ. Org. Lett. 2006; 8: 2191
- 19 Ahmed A, Hoegenauer EK, Enev VS, Hanbauer M, Kaehlig H, Ohler E, Mulzer J. J. Org. Chem. 2003; 68: 3026
- 20 Burova SA, McDonald FE. J. Am. Chem. Soc. 1991; 126: 2495
- 21a Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
- 21b Dess DB, Martin JC. J. Am. Chem. Soc. 1991; 113: 7277
- 22 Bal BS, Childers WE. Jr, Pinnick HW. Tetrahedron 1981; 37: 2091
- 23 Caroll FI, Abraham P, Pitner JB, Jablonski SD, Singh P, Kwon YW, Triggle DJ. J. Chem. Soc., Chem. Commun. 1992; 795
- 24 Hunt JA, Roush WR. J. Am. Chem. Soc. 1996; 118: 9998
- 25 Griggs ND, Phillips AJ. Org. Lett. 2008; 10: 4955