Scalable Total Syntheses and Structure-Activity Relationships of Haouamines A, B, and Their Derivatives as Stable Formate Salts.

Friedel-Crafts cyclization haouamines macrocyclization structure-activity relationships “anti-Wacker”-type cyclization

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
01 Oct 2020
Historique:
received: 10 04 2020
pubmed: 16 4 2020
medline: 16 4 2020
entrez: 16 4 2020
Statut: ppublish

Résumé

Haouamines A, B, and their derivatives were synthesized via Suzuki-Miyaura coupling and three key cyclization reactions as follows: the newly developed palladium(0)-catalyzed arylative cyclization of phenylalanine-derived alkyne-aldehydes with 2-bromoarylboronic acid (an "anti-Wacker"-type cyclization); BF

Identifiants

pubmed: 32291830
doi: 10.1002/chem.202001756
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

12528-12532

Subventions

Organisme : Platform Project for Supporting Drug Discovery and Life Science Research from AMED
ID : JP19am0101095
Organisme : Platform Project for Supporting Drug Discovery and Life Science Research from AMED
ID : JP19am0101100
Organisme : The Research Foundation for Pharmaceutical Sciences
Organisme : SUNTRY FOUNDATION for LIFE SCIENCES
Organisme : JSPS KAKENHI
ID : 2459004

Informations de copyright

© 2020 Wiley-VCH GmbH.

Références

 
J. Clardy, C. Walsh, Nature 2004, 432, 829-837;
F. E. Koehn, G. T. Carter, Nat. Rev. Drug Discovery 2005, 4, 206-220;
J. W.-H. Li, J. C. Vederas, Science 2009, 325, 161-165;
D. J. Newman, G. M. Cragg, J. Nat. Prod. 2016, 79, 629-661.
L. Garrido, E. Zubía, M. J. Ortega, J. Salvá, J. Org. Chem. 2003, 68, 293-299.
N. Z. Burns, I. N. Krylova, R. N. Hannoush, P. S. Baran, J. Am. Chem. Soc. 2009, 131, 9172-9173.
 
Y. Momoi, K.-I. Okuyama, H. Toya, K. Sugimoto, K. Okano, H. Tokuyama, Angew. Chem. Int. Ed. 2014, 53, 13215-13219;
Angew. Chem. 2014, 126, 13431-13435;
K.-I. Okuyama, Y. Momoi, K. Sugimoto, K. Okano, H. Tokuyama, Synlett 2011, 73-76.
Total synthesis of haouamine A:
P. S. Baran, N. Z. Burns, J. Am. Chem. Soc. 2006, 128, 3908-3909;
N. Z. Burns, P. S. Baran, Angew. Chem. Int. Ed. 2008, 47, 205-208;
Angew. Chem. 2008, 120, 211-215;
N. Z. Burns, M. Jessing, P. S. Baran, Tetrahedron 2009, 65, 6600-6610; see also ref. [3].
Formal synthesis of haouamine A:
A. Fürstner, J. Ackerstraff, Chem. Commun. 2008, 2870-2872;
E. Fenster, C. Fehl, J. Aubé, Org. Lett. 2011, 13, 2614-2617;
J. H. Jeong, S. M. Weinreb, Org. Lett. 2006, 8, 2309-2312;
T. Taniguchi, H. Zaimoku, H. Ishibashi, J. Org. Chem. 2009, 74, 2624-2626.
Total synthesis of the originally reported structure of haouamine: B. M. Matveenko, G. Liang, E. M. W. Lauterwasser, E. Zubía, D. Trauner, J. Am. Chem. Soc. 2012, 134, 9291-9295.
A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722-6737;
Angew. Chem. 2011, 123, 6854-6869, and references therein.
 
N. D. Smith, J. Hayashida, V. H. Rawal, Org. Lett. 2005, 7, 4309-4312;
M. A. Grundl, D. Trauner, Org. Lett. 2006, 8, 23-25. see also ref. 6 e.
 
H. Tsukamoto, T. Ueno, Y. Kondo, J. Am. Chem. Soc. 2006, 128, 1406-1407;
H. Tsukamoto, T. Ueno, Y. Kondo, Org. Lett. 2007, 9, 3033-3036.
 
E. J. Corey, D. Y. Gin, R. S. Kania, J. Am. Chem. Soc. 1996, 118, 9202-9203;
B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946-5952. Et-DuPHOS as ligand did not work well in our system.
 
U. Schmidt, H. Griesser, V. Leitenberger, A. Lieberknecht, R. Mangold, R. Meyer, B. Riedl, Synthesis 1992, 487-490;
T. Noji, K. Okano, T. Fukuyama, H. Tokuyama, Org. Synth. 2011, 88, 388-397.
Crude aldehydes 10 a and 10 b, prepared by 1) tert-butyldimethylsilyl chloride (TBSCl), Et3N, dichloromethane; 2) LiAlH4, Et2O; 3) MnO2, Et2O from methyl 3,5-dihydroxybenzoates, were employed for HWE reaction.
M. L. uz Cardona, M. I. Fernandez, M. B. Garcia, J. R. Pedro, Tetrahedron 1986, 42, 2725-2730;
S. Radix, R. Barret, Tetrahedron 2007, 63, 12379-12387.
 
U. Schmidt, A. Lieberknecht, J. Wild, Synthesis 1984, 53-61;
M. Berwe, W. Jöntgen, J. Krüger, Y. Chancho-Grande, T. Lampe, M. Michels, H. Paulsen, S. Raddatz, S. Weigand, Org. Process Res. Dev. 2011, 15, 1348-1357;
H. Azuma, K. Okano, T. Fukuyama, H. Tokuyama, Org. Synth. 2011, 88, 152-161.
T. Tsunoda, J. Otsuka, Y. Yamamiya, S. Itô, Chem. Lett. 1994, 23, 539-542. The original procedure, in which N,N,N′,N′-tetramethylazodicarboxamide (TMAD) (1.5 equiv) was added all at once to a cold benzene solution of sulfonamide, alcohol, and PBu3, sometimes caused incomplete conversion and a loss of optical purity in our system due to increased viscosity and exothermic reaction. Modified procedure including a slow addition of PBu3 to a cold THF solution of sulfonamide, propargyl alcohol, and TMAD (1.2 equiv) with keeping internal temperature below 4 °C solved these problems.
It was reported that the alkynylation of N-tosylamide of chiral amino acid ester under Mitsunobu reaction conditions accompanied a partial racemization. S. E. Denmark, J. H.-C. Liu, J. M. Muhuhu, J. Org. Chem. 2011, 76, 201-215.
A small loss of optical purities would probably be ascribed to Pd/C-catalyzed reduction of a trace of E isomers contained in 9 a and 9 b.
H. G. Kuivila, L. E. Benjamin, C. J. Murphy, A. D. Price, J. H. Polevy, J. Org. Chem. 1962, 27, 825-829.
J. Liu, E. Muth, U. Flörke, G. Henkel, K. Merz, J. Sauvageau, E. Schwake, G. Dyker, Adv. Synth. Catal. 2006, 348, 456-462.
S. A. King, B. Pipik, A. S. Thompson, A. DeCamp, T. R. Verhoeven, Tetrahedron Lett. 1995, 36, 4563-4566.
 
T. Ohshima, Y. Xu, R. Takita, S. Shimizu, D. Zhong, M. Shibasaki, J. Am. Chem. Soc. 2002, 124, 14546-14547;
T. Ohshima, Y. Xu, R. Takita, M. Shibasaki, Tetrahedron 2004, 60, 9569-9588.
V. Wascholowski, K. R. Knudsen, C. E. T. Mitchell, S. Ley, Chem. Eur. J. 2008, 14, 6155-6165.
S. Niwayama, J. Org. Chem. 2000, 65, 5834-5836.
I. Minami, K. Takahashi, I. Shimizu, T. Kimura, J. Tsuji, Tetrahedron 1986, 42, 2971-2977.
A. Lujan-Montelongo, F. F. Fleming, Org. Synth. 2013, 90, 229-239.
T. Tsunoda, M. Suzuki, R. Noyori, Tetrahedron Lett. 1980, 21, 1357-1358.
J. Takagi, K. Takahashi, T. Ishiyama, N. Miyaura, J. Am. Chem. Soc. 2002, 124, 8001-8006. The preparation of 1-cyclohexenylboronic acid via Br-Li exchange is reported.
J.-T. Zhang, X.-L. Qi, J. Chen, B.-S. Li, Y.-B. Zhou, X.-P. Cao, J. Org. Chem. 2011, 76, 3946-3959.
 
S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1986, 27, 5541-5544;
J. M. Saá, M. Dopico, G. Martorell, A. Carcía-Raso, J. Org. Chem. 1990, 55, 991-995.
 
C. Simon, S. Hosztafi, S. Makleit, J. Heterocycl. Chem. 1997, 34, 349-365;
N. E. Golantsov, A. V. Karchava, M. A. Yurovskaya, Chem. Hetrocycl. Compd. 2008, 44, 263-294;
R. C. Bernotas, R. V. Cube, Tetrahedron Lett. 1991, 32, 161-164;
T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, H. Yamamoto, S. Ito, Tetrahedron Lett. 1996, 37, 2463-2466.
 
K. Narasaka, S. Yamazaki, Y. Ukaji, Chem. Lett. 1985, 14, 1177-1178;
E. J. Corey, P.-w. Yuen, Tetrahedron Lett. 1989, 30, 5825-5828.
 
G. Guikkena, D. J. Ramón, M. Yus, Chem. Rev. 2010, 110, 1611-1641;
I. A. Khan, A. K. Saxena, J. Org. Chem. 2013, 78, 11656-11669.
F. Zaragoza, H. Stephenson, J. Org. Chem. 2001, 66, 2518-2521.
M. D. Bezoari, A. Babin, J. Undergrad. Chem. Res. 2017, 16, 27.

Auteurs

Hirokazu Tsukamoto (H)

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
Department of Pharmaceutical Sciences, Yokohama University of Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama, 245-0066, Japan.

Saki Nakamura (S)

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.

Akito Tomida (A)

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.

Takayuki Doi (T)

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.

Classifications MeSH