Unified Total Synthesis of (-)-Enigmazole A and (-)-15-O-Methylenigmazole A.
gold-catalyzed reaction
macrocycles
natural products
tandem reaction
tetrahydropyrans
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
02 Nov 2020
02 Nov 2020
Historique:
received:
26
08
2020
pubmed:
10
9
2020
medline:
10
9
2020
entrez:
9
9
2020
Statut:
ppublish
Résumé
The total synthesis of cytotoxic marine phosphomacrolides, (-)-enigmazole A and (-)-15-O-methylenigmazole A, is described in detail. The 2,6-cis-substituted tetrahydropyran ring was efficiently elaborated by using a tandem olefin cross-metathesis/intramolecular oxa-Michael addition reaction. The 18-membered macrolactone skeleton was forged via a Au-catalyzed propargylic benzoate rearrangement/macrocyclic ring-closing metathesis sequence. Late-stage diversification of a common intermediate enabled unified total synthesis of (-)-enigmazole A and (-)-15-O-methylenigmazole A.
Identifiants
pubmed: 32902874
doi: 10.1002/asia.202001015
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3494-3502Subventions
Organisme : Kitasato University
Organisme : The Asahi Glass Foundation
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
N. Oku, K. Takada, R. W. Fuller, J. A. Wilson, M. L. Peach, L. K. Pannell, J. B. McMahon, K. R. Gustafson, J. Am. Chem. Soc. 2010, 132, 10278-10285.
I. Ohtani, T. Kusumi, Y. Kashiman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096.
Y. Nagai, T. Kusumi, Tetrahedron Lett. 1995, 36, 1853-1856;
T. Yabuuchi, T. Kusumi, J. Org. Chem. 2000, 65, 397-404.
C. K. Skepper, T. Quach, T. F. Molinski, J. Am. Chem. Soc. 2010, 132, 10286-10292.
C. J. Henrich, E. I. Goncharova, J. A. Wilson, R. S. Gardella, T. R. Johnson, J. B. McMahon, K. Takada, H. R. Bokesch, K. R. Gustafson, Chem. Biol. Drug Des. 2007, 69, 321-330.
S. Hirota, K. Isozaki, Y. Moriyama, K. Hashimoto, T. Nishida, S. Ishiguro, K. Kawano, M. Hanada, A. Kurata, M. Takeda, G. M. Tunio, Y. Matsuzawa, Y. Kanakura, Y. Shinomura, Y. Kitamura, Science 1998, 279, 577-580;
T. Furitsu, T. Tsujimura, T. Tono, H. Ikeda, H. Kitayama, U. Koshimizu, H. Sugahara, J. H. Butterfield, L. K. Ashman, Y. Kanayama, Y. Matsuzawa, Y. Kitamurra, Y. Kanakura, J. Clin. Invest. 1993, 92, 1736-1744.
Y. Ai, M. V. Kozytska, Y. Zou, A. S. Khartulyari, A. B. Smith III., J. Am. Chem. Soc. 2015, 137, 15426-15429;
Y. Ai, M. V. Kozytska, Y. Zou, A. S. Khartulyari, W. A. Maio, A. B. Smith III., J. Org. Chem. 2018, 83, 6110-6126.
A. Ahlers, T. de Haro, B. Gabor, A. Fürstner, Angew. Chem. Int. Ed. 2016, 55, 1406-1411;
Angew. Chem. 2016, 128, 1428-1433.
K. Sakurai, M. Sasaki, H. Fuwa, Angew. Chem. Int. Ed. 2018, 57, 5143-5146;
Angew. Chem. 2018, 130, 5237-5240.
A. Meissner, T. Kishi, Y. Fujisawa, Y. Murai, H. Takamura, I. Kadota, Tetrahedron Lett. 2018, 59, 4492-4495.
For reviews on Meyer-Schuster rearrangement of propargylic alcohols and relevant [3,3]-sigmatropic rearrangement of propargylic carboxylates, see:
D. A. Engel, G. B. Dudley, Org. Biomol. Chem. 2009, 7, 4149-4158;
V. Cadierno, P. Crochet, S. E. García-Garrido, J. Gimeno, Dalton Trans. 2010, 39, 4015-4031;
Y. Zhu, L. Sun, P. Lu, Y. Wang, ACS Catal. 2014, 4, 1911-1925.
For reviews on macrocyclic ring-closing metathesis, see:
A. Gradillas, J. Pérez-Castells, Angew. Chem. Int. Ed. 2006, 45, 6086-6101;
Angew. Chem. 2006, 118, 6232-6247;
A. Fürstner, Chem. Commun. 2011, 47, 6505-6511;
A. Fürstner, Science 2013, 341, 1229713;
A. H. Hoveyda, J. Org. Chem. 2014, 79, 4763-4792;
I. Cheng-Sánchez, F. Sarabia, Synthesis 2018, 50, 3749-3786.
H. Fuwa, K. Noto, M. Sasaki, Org. Lett. 2010, 12, 1636-1639;
H. Fuwa, T. Suzuki, H. Kubo, T. Yamori, M. Sasaki, Chem. Eur. J. 2011, 17, 2678-2688;
H. Fuwa, T. Noguchi, K. Noto, M. Sasaki, Org. Biomol. Chem. 2012, 10, 8108-8112. For a review, see:
H. Fuwa, M. Sasaki, Bull. Chem. Soc. Jpn. 2016, 89, 1403-1415.
For applications in total synthesis of natural products, see:
H. Fuwa, K. Noto, M. Sasaki, Heterocycles 2010, 82, 641-647;
H. Park, H. Kim, J. Hong, Org. Lett. 2011, 13, 3742-3745;
A. R. Waldeck, M. J. Krische, Angew. Chem. Int. Ed. 2013, 52, 4470-4473;
Angew. Chem. 2013, 125, 4566-4569;
B. M. Trost, C. E. Stivala, K. L. Hull, A. Huang, D. R. Fandrick, J. Am. Chem. Soc. 2014, 136, 88-91;
B. R. Kammari, N. K. Bejjanki, N. Kommu, Tetrahedron: Asymmetry 2015, 26, 296-303;
G. Wang, M. J. Krische, J. Am. Chem. Soc. 2016, 138, 8088-8091. For a review, see:
M. Sánchez-Roselló, J. Miró, C. del Pozo, Synthesis 2017, 49, 2787-2802.
P. L. Anelli, C. Biffi, F. Montanari, S. Quici, J. Org. Chem. 1987, 52, 2559-2562.
D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156;
D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
J. R. Parikh, W. v. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505-5507.
K. Omura, A. K. Sharma, D. Swern, J. Org. Chem. 1976, 41, 957-962;
A. J. Mancuso, D. Swern, Synthesis 1981, 165-184.
For details, see the Supporting Information.
P. J. Kocienski, C. Yeates, S. D. A. Steet, S. F. Campbell, J. Chem. Soc. Perkin Trans. 1 1987, 2183-2187.
C. H. Hong, Y. Kishi, J. Am. Chem. Soc. 1991, 113, 9693-9694.
T. Ichige, A. Miyake, N. Kanoh, M. Nakata, Synlett 2004, 1686-1690.
D. A. Evans, A. H. Hoveyda, J. Am. Chem. Soc. 1990, 112, 6447-6449.
Reducing hydroxy ketone 16 with NaBH(OAc)3 in CH3CN/AcOH (1 : 1) at −20 °C provided 1,3-anti-diol 8 quantitatively but with a moderate, 5 : 1 diastereoselectivity.
S. D. Rychnovsky, D. J. Skalitzky, Tetrahedron Lett. 1990, 31, 945-948.
S. Higashibayashi, K. Shinko, T. Ishizu, K. Hashimoto, M. Nakata, Synlett 2000, 1306-1308.
B. S. Bal, W. E. Childers Jr., H. W. Pinnick, Tetrahedron 1981, 37, 2091-2096;
G. A. Kraus, B. Roth, J. Org. Chem. 1980, 45, 4825-4830.
For recent examples, see:
J. Park, A. Jean, D. Y.-K. Chen, Angew. Chem. Int. Ed. 2017, 56, 14237-14240;
Angew. Chem. 2017, 129, 14425-14428;
J. Wang, W.-B. Sun, Y.-Z. Li, X. Wang, B.-F. Sun, G.-Q. Lin, J.-P. Zou, Org. Chem. Front. 2015, 2, 674-676;
D. M. Hodgson, E. P. A. Talbot, B. P. Clark, Chem. Commun. 2012, 48, 6349-6350;
D. M. Hodgson, E. P. A. Talbot, B. P. Clark, Org. Lett. 2011, 13, 5751-5753;
R. S. Ramón, S. Gaillard, A. M. Z. Slawin, A. Porta, A. D'Alfonso, G. Zanoni, S. P. Nolan, Organometallics 2010, 29, 3665-3668.
M. N. Pennell, P. G. Turner, T. D. Sheppard, Chem. Eur. J. 2012, 18, 4748-4758.
M. Egi, Y. Yamaguchi, N. Fujiwara, S. Akai, Org. Lett. 2008, 10, 1867-1870.
S. Bhuvaneswari, M. Jeganmohan, C.-H. Cheng, Chem. Asian J. 2010, 5, 141-146.
L. Yang, Q. Zeng, Synthesis 2017, 49, 3149-3156.
M. Yu, G. Li, S. Wang, L. Zhang, Adv. Synth. Catal. 2007, 349, 871-875.
H. Imagawa, Y. Asai, H. Takano, H. Hamagaki, M. Nishizawa, Org. Lett. 2006, 8, 447-450.
N. Marion, P. Carlqvist, R. Gealageas, P. de Frémont, F. Maseras, S. P. Nolan, Chem. Eur. J. 2007, 13, 6437-6451;
R. S. Ramón, N. Marion, S. P. Nolan, Tetrahedron 2009, 65, 1767-1773.
In this paper, this reaction is referred to as Au-catalyzed propargylic benzoate rearrangement due to its formal similarity with other Au-catalyzed propargylic carboxylate rearrangements. However, the Nolan's reaction has been suggested to proceed via a SN2′-like pathway and may not be a [3,3]-sigmatropic rearrangement. The exact mechanism of [(NHC)Au]-catalyzed reaction of propargylic carboxylates has not been firmly established yet.
E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 13, 3769-3772.
J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956.
The four-step sequence from 44 to 1 followed that described by Molinski et al.[4].
K. Takai, Y. Hotta, K. Oshima, H. Nozaki, Bull. Chem. Soc. Jpn. 1980, 53, 1698-1702;
L. Lombardo, Org. Synth. 1987, 65, 81-85.
E. Uhlmann, J. Engels, Tetrahedron Lett. 1986, 27, 1023-1026.
Y. Watanabe, T. Nakamura, H. Mitsumoto, Tetrahedron Lett. 1997, 38, 7407-7410.