Please do not adjust margins
ChemComm
Page 4 of 4
COMMUNICATION
Journal Name
Sigman, H. M. L. Davies and S. B. Blakey, Chem. Sci., 2016,
We thank the Zeon Corporation for the kind gift of CPME.
DOI: 10.1039/C7CC01514C
6687‐6691.
11 The reaction of 1n and 1o resulted in low yields. A small
amount of starting material remained unchanged, and
phosphorylated reaction intermediates were probably
formed.
Notes and references
1
2
For example, see: 5 membered cyclic ether derivatives; (a)
C.‐C. Liaw, F.‐R. Chang, Y.‐C. Wu, H.‐K. Wang, Y. Nakanishi, K.
F. Bastow and K.‐H. Lee, J. Nat. Prod., 2004, 67, 1804‐1808;
(b) M. A. Lawson, M. Kaouadji and A. J. Chulia, Tetrahedron
Lett., 2008, 49, 2407‐2409; (c) G.‐H. Tang, Z.‐W. Chen, T.‐T.
Lin, M. Tan, X.‐Y. Gao, J.‐M. Bao, Z.‐B. Cheng, Z.‐H. Sun, G.
Huang and S. Yin, J. Nat. Prod., 2015, 78, 1894‐1903.
For example, see: 6 membered cyclic ether derivatives; (a) L.
Ghribi, P. Waffo‐Téguo, S. Cluzet, A. Marchal, J. Marques, J.‐
M. Mérillon and H. B. Jannet, Bioorg. Med. Chem. Lett., 2015,
25, 3825‐3830; (b) S. A. Ahmed, S. A. Ross, D. Slade, M. M.
Radwan, I. A. Khan and M. A. Elsohly, Phytochemistry, 2015,
117, 194‐199; (c) J. Le, W. Lu, X. Xiong, Z. Wu and W. Chen,
Molecules, 2015, 20, 18496‐18510.
12 The cyclization of 1n or 1o at 80 °C gave 53% of 2n or 35% of
2o. The elebvated reaction temperature slightly improved
the yields, but they are unsatisfactory.
13 The reaction of 1‐decanol in the presence of PO(OMe)3 and
NaH never produced didecyl ether as a symmetric ether
formed by the intermolecular coupling.
14 Compounds 3, 4 and 5 could be alternatively prepared using
POCl(OMe)2. See Supporting Information.
15 The use of NaH in the absence of MeOH also gave 2a in low
yields (10‐14%). The contaminated H2O probably facilitates
3
4
For example, see: 6 membered cyclic ether derivatives; K. Li,
X.‐M. Li, N.‐Y. Ji and B.‐G. Wang, J. Nat. Prod., 2008, 71, 28‐
30.
the conversion of
Scheme 2.
4 and 5 into 3’ derivative as shown in
(a) T. Shibata, R. Fujiwara and Y. Ueno, Synlett, 2005, 152‐
154; (b) X. Jiang, E. K. London, D.J. Morris, G. J. Clarkson and
M. Wills, Tetrahedron, 2010, 66, 9828‐9834; (c) I. Čorić, J. H.
Kim, T. Vlaar, M. Patil, W. Thiel and B. List, Angew. Chem. Int.
Ed., 2013, 52, 3490‐3493; (d) J. Kim, D.‐H. Lee, N.
Kalutharage and C. S. Yi, ACS catal. , 2014, 4, 3881‐3885; (e)
M. Hellal, F. C. Falk, E. Wolf, M. Dryzhakov and J. Moran, Org.
Biomol. Chem., 2014, 12, 5990‐5994; (f) A. Bunrit, C.
Dahlstrand, S. K. Olsson, P. Srifa, G. Huang, A. Orthaber, P. J.
R. Sjöberg, S. Biswas, F. Himo and J. S. M. Samec, J. Am.
Chem. Soc., 2015, 137, 4646‐4649.
5
(a) H. Aikawa, S. Tago, K. Umetsu, N. Haginiwa and N. Asao,
Tetrahedron, 2009, 65, 1774‐1784; (b) K. Yoshikawa, T.
Nagata, T. Yoshino, Y. Nakamoto, N. Haginoya, R. Muto, A.
Mochizuki, H. Kanno and T. Ohta, Heterocycles, 2012, 85
,
1711‐1720; (c) B. D. Kelly and T. H. Lambert, Org. Lett., 2011,
13, 740‐743; (d) P. H. Huy and A. M. P. Koskinen, Org. Lett.,
2013, 15, 5178‐5181.
6
7
8
F. Aric
ChemSusChem, 2012,
S. Asai, M. Kato, Y. Monguchi, H. Sajiki and Y. Sawama,
ChemistrySelect, 2017, , 876‐878.
ò
, P. Tundo, A. Maranzana and G. Tonachini,
5, 1578‐1586.
2
(a) K. Watanabe, N. Yamagiwa and Y. Torisawa, Org. Process
Res., 2007, 11, 251‐258; b) Y. Monguchi, K. Kitamoto, T.
Ikawa, T. Maegawa and H. Sajiki, Adv. Synth. Catal., 2008,
350, 2767‐2777; (c) K. Watanabe, N. Kogoshi, H. Miki and Y.
Torisawa, Synth. Commun., 2009, 39, 2008‐2013; d) V.
Antonucci, J. Coleman, J. B. Ferry, N. Johnson, M. Mathe, J. P.
Scott and J. Xu, Org. Process Res., 2011, 15, 939‐941; e) S.
Kobayashi, H. Kuroda, Y. Ohtsuka, T. Kashihara, A. Masuyama
and K. Watanabe, Tetrahedron, 2013, 69, 2251‐2259; f) K.
Watanabe, Molecules, 2013, 18, 3183‐3194.
9
(a) X. Xu, F. Song, S. Wang, S. Li, F. Xiao, J. Zhao, Y. Yang, S.
Shang, L. Yang and J. Shi, J. Nat. Prod., 2004, 67, 1661‐1666;
(b) M. Otomo, K. Takahashi, H. Miyoshi, K. Osada, H.
Nakashima and N. Yamaguchi, Biol. Pharm. Bull., 2008, 31
,
1489‐1495; (c) R. Khan, A. Malik, M. I. Qadir, A. Adhikari and
M. I. Choudhary, Chem. Nat. Compd., 2010, 46, 722‐725.
10 (a) J. D. Harden, J. V. Ruppel, G.‐Y. Gao and X. P. Zhang, Chem.
Commun., 2007, 4644‐4646; (b) X. Guo, S. Pan, J. Liu and Z. Li,
J. Org. Chem., 2009, 74, 8848‐8851; (c) M. V. Pham and N.
Cramer, Angew. Chem. Int. Ed., 2014, 53, 3484‐3487; (d) S.
Asai, Y. Yabe, R. Goto, S. Nagata, Y. Monguchi, Y. Kita, H.
Sajiki and Y. Sawama, Chem. Pharm. Bull., 2015, 63, 757‐761;
(e) N. M. Weldy, A. G. Schafer, C. P. Owens, C. J. Herting, A.
Varela‐Alvarez, S. Chen, Z. Niemeyer, D. G. Musaev, M. S.
4 | J. Name., 2012, 00, 1‐3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins