Total Synthesis of the Proposed Structure of Neaumycin B.
Antitumor Agents
C−C Coupling
Macrolide Natural Products
Spiroketalization
Total Synthesis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
18 Dec 2023
18 Dec 2023
Historique:
received:
06
09
2023
pubmed:
27
10
2023
medline:
27
10
2023
entrez:
27
10
2023
Statut:
ppublish
Résumé
The total synthesis of the proposed structure of anti-glioblastoma natural product neaumycin B was achieved in 22 steps (longest linear sequence). The synthesis features HCl-mediated [6,6]-spiroketalization, a combination of Krische iridium-catalyzed crotylation, Marshall palladium-catalyzed propargylation, Fürstner nickel-catalyzed regio- and enantioselective vicinal monoprotected diol formation, Brown crotylation and asymmetric halide-aldehyde cycloaddition, so as to establish the challenging contiguous stereocenters.
Identifiants
pubmed: 37889502
doi: 10.1002/anie.202313186
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202313186Subventions
Organisme : National Natural Science Foundation of China
ID : 82273794
Organisme : National Natural Science Foundation of China
ID : 82073695
Organisme : National Natural Science Foundation of China
ID : 82273808
Organisme : Frontiers Science Center for New Organic Matter
ID : 63181206
Organisme : Hundred Young Academic Leaders Program of Nankai University
ID : 63233023
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
S. Huang, X. Wang, Y. Yan, J. Wang, J. Zhang, C. Liu, W. Xiang, B. Shen, Org. Lett. 2012, 14, 1254-1257.
M. Simone, S. I. Maffioli, A. Tocchetti, S. Tretter, M. Cattaneo, I. Biunno, E. Gaspari, S. Donadio, J. Antibiot. 2015, 68, 406-408.
M. C. Kim, H. Machado, K. H. Jang, L. Trzoss, P. R. Jensen, W. Fenical, J. Am. Chem. Soc. 2018, 140, 10775-10784.
Q. T. Ostrom, L. Bauchet, F. G. Davis, I. Deltour, J. L. Fisher, C. E. Langer, M. Pekmezci, J. A. Schwartzbaum, M. C. Turner, K. M. Walsh, M. R. Wrensch, J. S. Barnholtz-Sloan, Neurooncology 2014, 16, 896-913.
P. Northcott, Nature 2017, 547, 291-292.
F. Ringel, H. Pape, M. Sabel, D. Krex, H. C. Bock, M. Misch, A. Weyerbrock, T. Westermaier, C. Senft, P. Schucht, B. Meyer, M. Simon, Neurooncology 2016, 18, 96-104;
W. Wu, J. L. Klockow, M. Zhang, F. Lafortune, E. Chang, L. Jin, Y. Wu, H. E. Daldrup-Link, Pharmacol. Res. 2021, 171, 105780.
www.chictr.org.cn, register number: ChiCTR2000035315;
ClinicalTrials.gov, NCT number: NCT05053880;
www.anzctr.org.au, Trial ID: ACTRN12621001172897.
H. Takeshita, T. Sugai, H. Fuwa, J. Org. Chem. 2021, 86, 6787-6799;
Y. M. Pyun, S. I. Cho, S. J. Lee, D. H. Lee, Bull. Korean Chem. Soc. 2022, 43, 1364-1366;
X. Liang, M. Yoo, T. Schempp, S. Maejima, M. J. Krische, Angew. Chem. Int. Ed. 2022, 61, e202214786;
T. Sugai, H. Fuwa, Synthetic Studies on Neaumycin B: Stereoselective Synthesis of the Northern Hemisphere Spiroacetal, a conference abstract of the Chemical Society of Japan, 2020, 2 H5-35 A.
J. Ding, A. B. Smith, J. Am. Chem. Soc. 2023, 145, 18240-18246.
A. T. Khan, E. Mondal, Synlett 2003, 5, 0694-0698;
C.-E. Yeom, Y. J. Kim, S. Y. Lee, Y. J. Shin, B. M. Kim, Tetrahedron 2005, 61, 12227-12237.
For reviews:
J. M. Ketcham, I. Shin, T. P. Montgomery, M. J. Krische, Angew. Chem. Int. Ed. 2014, 53, 9142-9150;
S. W. Kim, W. Zhang, M. J. Krische, Acc. Chem. Res. 2017, 50, 2371-2380;
M. Holmes, L. A. Schwartz, M. J. Krische, Chem. Rev. 2018, 118, 6026-6052;
R. S. Doerksen, C. C. Meyer, M. J. Krische, Angew. Chem. Int. Ed. 2019, 58, 14055-14064; For representative research works:
X. Gao, H. Han, M. J. Krische, J. Am. Chem. Soc. 2011, 133, 12795-12800;
J. Moran, A. Preetz, R. A. Mesch, M. J. Krische, Nat. Chem. 2011, 3, 287-290;
S. B. Han, A. Hassan, I. S. Kim, M. J. Krische, J. Am. Chem. Soc. 2010, 132, 15559-15561;
Y. Lu, S. K. Woo, M. J. Krische, J. Am. Chem. Soc. 2011, 133, 13876-13879;
D. J. Del Valle, M. J. Krische, J. Am. Chem. Soc. 2013, 135, 10986-10989.
J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214-8219;
J. A. Marshall, H. R. Chobanian, M. M. Yanik, Org. Lett. 2001, 3, 3369-3372;
B. M. Trost, W.-J. Bai, C. E. Stivala, C. Hohn, C. Poock, M. Heinrich, S. Xu, J. Rey, J. Am. Chem. Soc. 2018, 140, 17316-17326.
T. Q. Davies, J. J. Murphy, M. Dousset, A. Fürstner, J. Am. Chem. Soc. 2021, 143, 13489-13494;
M. Kimura, A. Ezoe, M. Mori, K. Iwata, Y. Tamaru, J. Am. Chem. Soc. 2006, 128, 8559-8568.
H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092-2093;
H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 5919-5923;
A. B. Smith, K. P. Minbiole, P. R. Verhoest, M. Schelhaas, J. Am. Chem. Soc. 2001, 123, 10942-10953;
Y. Feng, J. Liu, Y. P. Carrasco, J. B. MacMillan, J. K. De Brabander, J. Am. Chem. Soc. 2016, 138, 7130-7142.
C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352-5353;
X. Shen, A. S. Wasmuth, J. Zhao, C. Zhu, S. G. Nelson, J. Am. Chem. Soc. 2006, 128, 7438-7439.
For representative reviews:
M. M. Heravi, E. Hashemi, Tetrahedron 2012, 68, 9145-9178;
M. M. Heravi, M. Malmir, R. Moradi, Curr. Org. Chem. 2019, 23, 2469-2488; For representative research works:
F. Glaus, K.-H. Altmann, Angew. Chem. Int. Ed. 2015, 54, 1937-1940;
L. Wang, Q. Yu, W. Zhang, S. Yang, L. Peng, L. Zhang, X. Li, F. Gagosz, A. Kirschning, J. Am. Chem. Soc. 2022, 144, 6871-6881.
For representative reviews:
F. Perron, K. F. Albizati, Chem. Rev. 1989, 89, 1617-1661;
J. E. Aho, P. M. Pihko, T. K. Rissa, Chem. Rev. 2005, 105, 4406-4440;
F. Zhang, S. Zhang, Y. Tu, Nat. Prod. Rep. 2018, 35, 75-104; For representative research works:
D. A. Evans, S. W. Kaldor, T. K. Jones, J. Clardy, T. J. Stout, J. Am. Chem. Soc. 1990, 112, 7001-7031;
D. A. Evans, H. P. Ng, D. L. Rieger, J. Am. Chem. Soc. 1993, 115, 11446-11459;
D. A. Evans, A. M. Ratz, B. E. Huff, G. S. Sheppard, J. Am. Chem. Soc. 1995, 117, 3448-3467;
M. Tortosa, N. A. Yakelis, W. R. Roush, J. Am. Chem. Soc. 2008, 130, 2722-2723.
For representative reviews:
M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448-2462;
D. Pflästerer, A. S. K. Hashmi, Chem. Soc. Rev. 2016, 45, 1331-1367;
Z. Lu, T. Li, S. R. Mudshinge, B. Xu, G. B. Hammond, Chem. Rev. 2021, 121, 8452-8477; For representative research works:
B. M. Trost, B. M. O'Boyle, J. Am. Chem. Soc. 2008, 130, 16190-16192;
B. M. Trost, B. M. O'Boyle, D. Hund, J. Am. Chem. Soc. 2009, 131, 15061-15074;
S. Newton, C. F. Carter, C. M. Pearson, L. de C Alves, H. Lange, P. Thansandote, S. V. Ley, Angew. Chem. Int. Ed. 2014, 53, 4915-4920;
A. Sokolsky, M. Cattoen, A. B. Smith, Org. Lett. 2015, 17, 1898-1901;
B. M. Trost, Y. Wang, A. K. Buckl, Z. Huang, M. H. Nguyen, O. Kuzmina, Science 2020, 368, 1007-1011.
K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408-7410;
L. A. Wessjohann, G. Scheid, Synthesis 1999, 1-36.
D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636-3638;
A. B. Smith, S. M. Condon, J. A. McCauley, J. L. Leazer Jr, J. W. Leahy, R. E. Maleczka Jr, J. Am. Chem. Soc. 1995, 117, 5407-5408;
M. H. Becker, P. Chua, R. Downham, C. J. Douglas, N. K. Garg, S. Hiebert, S. Jaroch, R. T. Matsuoka, J. A. Middleton, F. W. Ng, L. E. Overman, J. Am. Chem. Soc. 2007, 129, 11987-12002;
A. Fürstner, J.-A. Funel, M. Tremblay, L. C. Bouchez, C. Nevado, M. Waser, J. Ackerstaff, C. C. Stimson, Chem. Commun. 2008, 2873-2875.
For representative review:
B. Chatterjee, S. Bera, D. Mondal, Tetrahedron: Asymmetry 2014, 25, 1-55; For representative research works:
B. M. Trost, J. D. Chisholm, S. T. Wrobleski, M. Jung, J. Am. Chem. Soc. 2002, 124, 12420-12421;
A. B. Smith, S. Dong, J. B. Brenneman, R. J. Fox, J. Am. Chem. Soc. 2009, 131, 12109-12111.
Y. Okude, S. Hirano, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 1977, 99, 3179-3181;
H. Jin, J. Uenishi, W. J. Christ, Y. Kishi, J. Am. Chem. Soc. 1986, 108, 5644-5646;
K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Utimoto, H. Nozaki, J. Am. Chem. Soc. 1986, 108, 6048-6050;
X. Liu, X. Li, Y. Chen, Y. Hu, Y. Kishi, J. Am. Chem. Soc. 2012, 134, 6136-6139;
V. P. Kumar, Y. Kishi, J. Am. Chem. Soc. 2020, 142, 14743-14749; For representative reviews:
A. Fürstner, Chem. Rev. 1999, 99, 991-1046;
A. Gil, F. Albericio, M. Álvarez, Chem. Rev. 2017, 117, 8420-8446.
T. R. Hoye, C. S. Jeffrey, F. Shao, Nat. Protoc. 2007, 2, 2451-2458.
Deposition number 2290352 contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
K. Liu, R. E. Taylor, R. Kartika, Org. Lett. 2006, 8, 5393-5395;
R. Kartika, R. E. Taylor, Angew. Chem. Int. Ed. 2007, 46, 6874-6877;
K. Liu, J. W. Arico, R. E. Taylor, J. Org. Chem. 2010, 75, 3953-3957;
E. Stefan, R. E. Taylor, Org. Lett. 2012, 14, 3490-3493.
E. Nakamura, T. Inubushi, S. Aoki, D. Machi, J. Am. Chem. Soc. 1991, 113, 8980-8982.
S. D. Rychnovsky, B. N. Rogers, T. I. Richardson, Acc. Chem. Res. 1998, 31, 9-17.
A. L. Moure, R. G. Arrayás, D. J. Cárdenas, I. Alonso, J. C. Carretero, J. Am. Chem. Soc. 2012, 134, 7219-7222;
J. K. Park, B. A. Ondrusek, D. T. McQuade, Org. Lett. 2012, 14, 4790-4793;
P. Liu, Y. Fukui, P. Tian, Z. He, C. Sun, N. Wu, G. Lin, J. Am. Chem. Soc. 2013, 135, 11700-11703;
H. Yoshida, Y. Takemoto, K. Takaki, Asian J. Org. Chem. 2014, 3, 1204-1209;
D. V. Reddy, G. Sabitha, T. P. Rao, J. S. Yadav, Org. Lett. 2016, 18, 4202-4205.
K. Mori, K. Tanida, Tetrahedron 1981, 37, 3221-3225;
H. Toshima, T. Suzuki, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1989, 30, 6725-6728.
A. B. Smith III, V. A. Doughty, Q. Lin, L. Zhuang, M. D. McBriar, A. M. Boldi, W. H. Moser, N. Murase, K. Nakayama, M. Sobukawa, Angew. Chem. Int. Ed. 2001, 40, 191-195;
M. Ball, M. J. Gaunt, D. F. Hook, A. S. Jessiman, S. Kawahara, P. Orsini, A. Scolaro, A. C. Talbot, H. R. Tanner, S. Yamanoi, S. V. Ley, Angew. Chem. Int. Ed. 2005, 44, 5433-5438.
W. D. Emmons, A. S. Pagano, J. Am. Chem. Soc. 1955, 77, 89-92;
B. A. McKittrick, B. Ganem, Tetrahedron Lett. 1985, 26, 4895-4898;
K. V. Chuang, C. Xu, S. E. Reisman, Science 2016, 353, 912-915.
P. L. Anelli, C. Biffi, F. Montanari, S. Quici, J. Org. Chem. 1987, 52, 2559-2562.
H. Meerwein, P. Borner, O. Fuchs, H. J. Sasse, H. Schrodt, J. Spille, Chem. Ber. 1956, 89, 2060-2079.
D. W. Hart, J. Schwartz, J. Am. Chem. Soc. 1974, 96, 8115-8116.
D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129;
D. A. Evans, H. P. Ng, J. S. Clark, D. L. Rieger, Tetrahedron 1992, 48, 2127-2142; L. C. Dias, L. G. de Oliveira, M. A.
de Sousa, Org. Lett. 2003, 5, 265-268;
D. R. Williams, A. A. Kiryanov, U. Emde, M. P. Clark, M. A. Berliner, J. T. Reeves, Proc. Natl. Acad. Sci. USA 2004, 101, 12058-12063.
E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551-5553; For representative reviews:
L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784;
E. J. Corey, C. J. Helal, Angew. Chem. Int. Ed. 1998, 37, 1986-2012.
J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993;
M. H. Nguyen, M. Imanishi, T. Kurogi, A. B. Smith, J. Am. Chem. Soc. 2016, 138, 3675-3678;
P. A. Wender, C. T. Hardman, S. Ho, M. S. Jeffreys, J. K. Maclaren, R. V. Quiroz, S. M. Ryckbosch, A. J. Shimizu, J. L. Sloane, M. C. Stevens, Science 2017, 358, 218-223.
S. A. Frank, H. Chen, R. K. Kunz, M. J. Schnaderbeck, W. R. Roush, Org. Lett. 2000, 2, 2691-2694.