Organic Letters
Letter
(c) Williams, D. R.; Turske, R. A. Org. Lett. 2000, 2, 3217−3220.
(d) Zhang, Q.; Rivkin, A.; Curran, D. P. J. Am. Chem. Soc. 2002, 124,
5774−5781. (e) Furstner, A.; Feyen, F.; Prinz, H.; Waldmann, H.
Angew. Chem., Int. Ed. 2003, 42, 5361−5364. (f) Williams, D. R.;
Kammler, D. C.; Donnell, A. F.; Goundry, W. R. F. Angew. Chem., Int.
Ed. 2005, 44, 6715−6718. (g) Jessen, H. J.; Barbaras, D.; Hamburger,
M.; Gademann, K. Org. Lett. 2009, 11, 3446−3449. (h) Jessen, H. J.;
Schumacher, A.; Schmid, F.; Pfaltz, A.; Gademann, K. Org. Lett. 2011,
13, 4368−4370.
2004, 43, 4341−4345. (c) Miyashita, K.; Tsunemi, T.; Hosokawa, T.;
Ikejiri, M.; Imanishi, T. J. Org. Chem. 2008, 73, 5360−5370.
(3) (a) Basyouni, S. H. E.; Brewer, D.; Vining, L. C. Can. J. Bot. 1968,
46, 441−448. (b) McInnes, A. G.; Smith, D. G.; Wat, C. K.; Vining, L.
C.; Wright, J. L. C. J. Chem. Soc., Chem. Commun. 1974, 281−282.
(c) Cheng, Y.; Schneider, B.; Riese, U.; Schubert, B.; Li, Z.;
Hamburger, M. J. Nat. Prod. 2004, 67, 1854−1858. (d) Schmidt, K.;
Riese, U.; Li, Z.; Hamburger, M. J. Nat. Prod. 2003, 66, 378−383.
(e) Takahashi, S.; Kakinuma, N.; Uchida, K.; Hashimoto, R.;
Yanagisawa, T.; Nakagawa, A. J. Antibiot. 1998, 51, 596−598.
(4) (a) Halo, L. M.; Heneghan, M. N.; Yakasai, A. A.; Song, Z.;
Williams, K.; Bailey, A .M.; Cox, R. J.; Lazarus, C. M.; Simpson, T. J. J.
Am. Chem. Soc. 2008, 130, 17988−17996. (b) Yakasai, A. A.; Davison,
J.; Vasil, Z.; Halo, L. M.; Butts, C. P.; Bailey, A. M.; Simpson, J.; Cox,
R. J. J. Am. Chem. Soc. 2011, 133, 10990−10998. (c) Weber, T.; Laiple,
K. J.; Pross, E. K.; Textor, A.; Grond, S.; Welzel, K.; Pelzer, S.; Vente,
A. A.; Wohlleben, W. Chem. Biol. 2008, 15, 175−188.
(5) (a) Cheng, Y.; Schneider, B.; Riese, U.; Schubert, B.; Li, Z.;
Hamburger, M. J. Nat. Prod. 2006, 69, 436−438. (b) Schmidt, K.;
Gunther, W.; Stoyanova, S.; Schubert, B.; Li, Z.; Hamburger, M. Org.
Lett. 2002, 4, 197−199. (c) Isaka, M.; Chinthanom, P.; Supothina, S.;
Tobwor, P.; Hywel-Jones, N. L. J. Nat. Prod. 2010, 73, 2057−2060.
(d) Ma, C.; Li, Y.; Niu, S.; Zhang, H.; Liu, X.; Che, Y. J. Nat. Prod.
2011, 74, 32−37.
(6) Williams, D. R.; Kammler, D. C.; Donnell, A. F.; Goundry, W. R.
F. Angew. Chem., Int. Ed. 2005, 44, 6715−6718.
(7) Jessen, H. J.; Schumacher, A.; Shaw, T.; Pfaltz, A.; Gademann, K.
Angew. Chem., Int. Ed. 2011, 50, 4222−4226.
(8) (a) Williams, D. R.; Bremmer, M. L.; Brown, D. L.; D’Antuono, J.
J. Org. Chem. 1985, 50, 2809−2810. (b) Nielsen, A. T.; Houlihan, W. J.
Org. React. 1968, 16, 1−438. (c) Mukaiyama, T. Org. React. 1982, 28,
203−331. (d) Mahrwald, R. Modern Aldol Reactions; Wiley-VCH:
Weinheim, Germany, 2004.
(9) Review: (a) Snieckus, V. Chem. Rev. 1990, 90, 879−933.
(b) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem.,
Int. Ed. 2004, 43, 2206−2225.
(10) C5-substituted alcohol 16a was observed when the reaction was
treated with 3.0 equiv of t-BuLi.
(11) We also performed the DoM reaction with 16 using CeCl3
protocol during the optimization stage for this reaction under various
conditions. Unfortunately, only a trace amount of desired product was
obtained and the deprotection of one of the MOM groups resulted in
the formation of major side product. (a) Yamashita, S.; Iso, K.;
Kitajima, K.; Himuro, M.; Hirama, M. Tetrahedron Lett. 2009, 50,
3277−3279. (b) Yamashita, S.; Kitajima, K.; Iso, K.; Hirama, M. J. Org.
Chem. 2011, 76, 2408−2425.
(12) For synthetic routes and procedures, see the Supporting
Information. Selected examples for synthesis of aldehyde (2R,4R)-18:
(a) Organ, M. G.; Bilokin, Y. V.; Bratovanov, S. J. Org. Chem. 2002, 67,
5176−5183. (b) Leonard, W. R.; Belyk, K. M.; Bender, D. R.; Conlon,
D. A.; Hughes, D. L.; Reider, P. J. Org. Lett. 2002, 4, 4201−4204.
(c) Negishi, E. I.; Tan, Z.; Liang, B.; Novak, T. Proc. Natl. Acad. Sci.
U.S.A. 2004, 101, 5782−5787.
(13) For synthetic routes and procedures, see the Supporting
Information. Selected examples for synthesis of alcohol (2R)-20:
(a) Panek, J. S.; Jain, N. F. J. Org. Chem. 2001, 66, 2747−2756.
(b) Komatsu, K.; Tanino, K.; Miyashita, M. Angew. Chem., Int. Ed.
D
dx.doi.org/10.1021/ol402820d | Org. Lett. XXXX, XXX, XXX−XXX