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ChemComm
We are grateful for financial support from the NSFC
21172150, 21321061, 21290180), the NCET (12SCU-NCET-12-
3), and the Sichuan University 985 project. The authors also
7 Y. Ogawa, P. P. Painter, D. J. Tantillo and P. A. Wender, J. Org. Chem.,
2013, 78, 104.
(
0
8
The product, in which the R group falls on the same side as the
incorporated aldehyde, is assigned to have a Z configuration.
thank Prof. Richard P. Hsung (UW, Madison) for invaluable
discussions.
9 For selected examples, see: (a) J. H. Babler and W. J. Buttner,
Tetrahedron Lett., 1976, 17, 239; (b) G. E. Heasley, D. A. Smith and
J. N. Smith, J. Org. Chem., 1980, 45, 5206; (c) T. Nguyen Van and
N. De Kimpe, Tetrahedron, 2000, 56, 7969.
Notes and references
1
10 The product, in which the CH
the incorporated aldehyde, is assigned to have an E configuration.
For recent reviews on Prins cyclization, see: (a) L. E. Overman and 11 T. Mandai, J. Nokami, T. Yano, Y. Yoshinaga and J. Otera, J. Org.
L. D. Pennington, J. Org. Chem., 2003, 68, 7143; (b) E. A. Crane and Chem., 1984, 49, 172.
K. A. Scheidt, Angew. Chem., Int. Ed., 2010, 49, 8316; (c) X. Han, 12 K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem. Soc., 1972,
G. R. Peh and P. E. Floreancig, Eur. J. Org. Chem., 2013, 1193; 94, 4374.
d) S. J. Greco, R. G. Fiorot, V. Lacerda and R. B. dos Santos, 13 (a) S. Marumoto, J. J. Jaber, J. P. Vitale and S. D. Rychnovsky, Org.
2
Br group falls on the opposite side to
(
Aldrichimica Acta, 2013, 46, 59.
For selected progresses besides ref. 13 and 14, see: (a) J. Yang,
G. S. Viswanathan and C. J. Li, Tetrahedron Lett., 1999, 40, 1627;
Lett., 2002, 4, 3919. For selected advances of Prins cyclization from
this group, see: (b) D. J. Kopecky and S. D. Rychnovsky, J. Am. Chem.
Soc., 2001, 123, 8420; (c) J. E. Dalgard and S. D. Rychnovsky, J. Am.
Chem. Soc., 2004, 126, 15662; (d) R. Jasti, J. Vitale and S. D.
Rychnovsky, J. Am. Chem. Soc., 2004, 126, 9904; (e) R. Jasti, C. D.
Anderson and S. D. Rychnovsky, J. Am. Chem. Soc., 2005, 127, 9939;
( f ) K. Tadpetch and S. D. Rychnovsky, Org. Lett., 2008, 10, 4839;
(g) K. B. Bahnck and S. D. Rychnovsky, J. Am. Chem. Soc., 2008,
130, 13177; (h) V. Malathong and S. D. Rychnovsky, Org. Lett., 2009,
11, 4220; (i) M. R. Gesinski, K. Tadpetch and S. D. Rychnovsky, Org.
Lett., 2009, 11, 5342; ( j) M. R. Gesinski and S. D. Rychnovsky, J. Am.
Chem. Soc., 2011, 133, 9727; (k) G. C. Tay, M. R. Gesinski and S. D.
Rychnovsky, Org. Lett., 2013, 15, 4536; (l) G. C. Tay, C. Y. Huang and
S. D. Rychnovsky, J. Org. Chem., 2014, 79, 8733.
2
(
(
(
b) H. Huang and J. S. Panek, J. Am. Chem. Soc., 2000, 122, 9836;
c) P. A. Wender and A. J. Schrier, J. Am. Chem. Soc., 2011, 133, 9228;
d) J. M. Tenenbaum, W. J. Morris, D. W. Custar and K. A. Scheidt,
Angew. Chem., Int. Ed., 2011, 50, 5892; (e) K. Zheng, X. H. Liu, S. Qin,
M. S. Xie, L. L. Lin, C. W. Hu and X. M. Feng, J. Am. Chem. Soc., 2012,
1
34, 17564; ( f ) V. M. Lombardo, C. D. Thomas and K. A. Scheidt,
Angew. Chem., Int. Ed., 2013, 52, 12910; (g) G. C. Tsui, L. P. Liu and
B. List, Angew. Chem., Int. Ed., 2015, 54, 7703.
(a) R. W. Alder, J. N. Harvey and M. T. Oakley, J. Am. Chem. Soc.,
3
4
2
002, 124, 4960; (b) R. Jasti and S. D. Rychnovsky, Org. Lett., 2006,
8, 2175.
For the isolation of (ꢀ)-exiguolide, see: (a) S. Ohta, M. M. Uy, 14 (a) K. P. Chan and T. P. Loh, Org. Lett., 2005, 7, 4491. For selected
M. Yanai, E. Ohta, T. Hirata and S. Ikegami, Tetrahedron Lett.,
006, 47, 1957. For total synthesis of exiguolide, see: (b) M. S.
Kwon, S. K. Woo, S. W. Na and E. Lee, Angew. Chem., Int. Ed.,
008, 47, 1733; (c) H. Fuwa and M. Sasaki, Org. Lett., 2010, 12, 584;
d) C. Cook, X. Guinchard, F. Liron and E. Roulland, Org. Lett., 2010,
2, 744; (e) E. A. Crane, T. P. Zabawa, R. L. Farmer and K. A. Scheidt,
advances of Prins cyclization from this group, see: (b) K. P. Chan and
T. P. Loh, Tetrahedron Lett., 2004, 45, 8387; (c) F. Liu and T. P. Loh,
Org. Lett., 2007, 9, 2063; (d) K. P. Chan, A. H. Seow and T. P. Loh,
Tetrahedron Lett., 2007, 48, 37; (e) K. P. Chan, Y. H. Ling and
T. P. Loh, Chem. Commun., 2007, 939; ( f ) X. H. Hu, F. Liu and
T. P. Loh, Org. Lett., 2009, 11, 1741; (g) H. Q. Luo, X. H. Hu and
T. P. Loh, Tetrahedron Lett., 2010, 51, 1041; (h) H. Li and T. P.
Loh, Org. Lett., 2010, 12, 2679; (i) B. Li, Y. C. Lai, Y. J. Zhao,
Y. H. Wong, Z. L. Shen and T. P. Loh, Angew. Chem., Int. Ed.,
2012, 51, 10619.
2
2
(
1
Angew. Chem., Int. Ed., 2011, 50, 9112; ( f ) H. Fuwa, T. Suzuki,
H. Kubo, T. Yamori and M. Sasaki, Chem. – Eur. J., 2011, 17, 2678;
(
2
g) C. Cook, F. Liron, X. Guinchard and E. Roulland, J. Org. Chem.,
012, 77, 6728; (h) H. Fuwa, K. Mizunuma, M. Sasaki, T. Suzuki and
H. Kubo, Org. Biomol. Chem., 2013, 11, 3442; (i) H. Z. Li, H. M. Xie, 15 For reviews, see: (a) T. P. Loh, in Science of Synthesis, ed.
Z. G. Zhang, Y. J. Xu, J. Lu, L. Gao and Z. L. Song, Chem. Commun.,
015, 51, 8484. For other synthetic studies, see: ( j) C. R. Reddy and
N. N. Rao, RSC Adv., 2012, 2, 7724.
For the latest review on the bryostatins, see: (a) K. J. Hale and
S. Manaviazar, Chem. – Asian J., 2010, 5, 704. For the latest total
synthesis of bryostatins, see: (b) Y. Lu, S. K. Woo and M. J. Krische,
J. Am. Chem. Soc., 2011, 133, 13876 and references therein.
(a) J. Lu, Z. L. Song, Y. B. Zhang, Z. B. Gan and H. Z. Li, Angew. Chem.,
H. Yamamoto, Georg Thieme Verlag Stuttgart, New York, 2004,
p. 413; (b) T. P. Loh and G. L. Chua, Activation of Reactions by
Lewis acid derived from Ga, In, Sb and Bi, in Advances in Organic
Synthesis, ed. A. ur-Rahman, 2005, 1, pp. 173–214, For latest inves-
tigations of In-centered Lewis acids, see: (c) L. G. Zhuo, J. J. Zhang
and Z. X. Yu, J. Org. Chem., 2012, 77, 8527; (d) L. G. Zhuo, Y. C. Shi
and Z. X. Yu, Asian J. Org. Chem., 2014, 3, 842; (e) L. G. Zhuo,
J. J. Zhang and Z. X. Yu, J. Org. Chem., 2014, 79, 3809.
2
5
6
Int. Ed., 2012, 51, 5367. For geminal bis(silyl) Prins cyclization without 16 I. Marek, C. Meyer and J. F. Normant, Org. Synth., 1997, 74, 194.
configurational control of the exocyclic alkene, see: (b) D. R. Williams, 17 R. W. Hoffmann, Chem. Rev., 1989, 89, 1841.
A´ . I. Morales-Ramos and C. M. Williams, Org. Lett., 2006, 8, 4393.
18 G. S. Hammond, J. Am. Chem. Soc., 1955, 77, 334.
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