RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2021; 32(18): 1865-1868
DOI: 10.1055/s-0040-1720383
DOI: 10.1055/s-0040-1720383
letter
Asymmetric Formal Synthesis of Trichodermamides B and C
This work was financially supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, 18K14867, 20K15956 to AK and 18H02096, 21H02069 to MA), and the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research, BINDS) from the Japan Agency for Medical Research and Development (AMED, 19am0101084 and 21am0101084) to MA.
Abstract
An asymmetric formal synthesis of trichodermamides B and C was achieved in 15 steps based on a tyrosine ester chiral-pool approach. Key features of this synthesis include stereoselective construction of a cis-1,2-oxazadecaline core by an acid-mediated tandem deprotection–intramolecular oxy-Michael reaction, oxime ether formation via an N-bromination–elimination sequence, and diene construction by a palladium-catalyzed demonomethylcarbonation.
Key words
trichodermamides - formal synthesis - chiral pool - cis-1,2-oxazadecaline - oxy-Michael reaction - palladiumSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720383.
- Supporting Information
Publikationsverlauf
Eingereicht: 18. Mai 2021
Angenommen nach Revision: 09. Juli 2021
Artikel online veröffentlicht:
21. Juli 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1 Garo E, Starks CM, Jensen PR, Fenical W, Lobkovsky E, Clardy J. J. Nat. Prod. 2003; 66: 423
- 2 Davis RA, Longden J, Avery VM, Healy PC. Bioorg. Med. Chem. Lett. 2008; 18: 2836
- 3 Zhu ML, Yang Z, Feng HM, Gan Q, Che Q, Zhu TJ, Gu QQ, Han BN, Li DH. RSC Adv. 2017; 7: 48019
- 4 Lu CD, Zakarian A. Angew. Chem. Int. Ed. 2008; 47: 6829
- 5 Mfuh AM, Zhang Y, Stephens DE, Vo AX. T, Arman HD, Larionov OV. J. Am. Chem. Soc. 2015; 137: 8050
- 6 Jans PE, Mfuh AM, Arman HD, Shaffer CV, Larionov OV, Mooberry SL. J. Nat. Prod. 2017; 80: 676
- 7 Wan X, Joullié MM. J. Am. Chem. Soc. 2008; 130: 17236
- 8 Tang R, Kimishima A, Ishida R, Setiawan A, Arai M. J. Nat. Med. 2020; 74: 153
- 9 Wan XB, Doridot G, Joullie MM. Org. Lett. 2007; 9: 977
- 10 Kimishima A, Saito H, Yamaguchi A, Arai M. Tetrahedron Lett. 2020; 61: 151412
- 11 Recently, Reisman and co-workers reported an asymmetric synthesis of structurally related tetrahydro-1,2-oxazine. Cowper NG. W, Hesse MJ, Chan KM, Reisman SE. Chem. Sci. 2020 11. 11897.
- 12 Hayashi T, Hagihara T, Konishi M, Kumada M. J. Am. Chem. Soc. 1983; 105: 7767
- 13 Hayashi T, Yamamoto A, Hagihara T. J. Org. Chem. 1986; 51: 723
- 14 Luche JL. J. Am. Chem. Soc. 1978; 100: 2226
-
15 The stereochemistry of allyl alcohol 21 and 22 was determined by NOESY after conversion of both compounds into the corresponding carbonate (see the Supporting Information).
- 16 Cha JS, Kwon OO, Kwon SY. Bull. Korean Chem. Soc. 1995; 16: 1009
- 17 Kocienski P, Narquizian R, Raubo P, Smith C, Farrugia LJ, Muir K, Boyle FT. J. Chem. Soc., Perkin Trans. 1 2000; 2357
- 18 Kunishima M, Kawachi C, Morita J, Terao K, Iwasaki F, Tani S. Tetrahedron 1999; 55: 13159
- 19 Legoff E. J. Org. Chem. 1964; 29: 2048
- 20 Tsuji J, Yamakawa T, Kaito M, Mandai T. Tetrahedron Lett. 1978; 19: 2075
- 21 Trost BM, Verhoeven TR, Fortunak JM. Tetrahedron Lett. 1979; 20: 2301
-
22 The palladium-catalyzed diene formation of the corresponding β-carbonate also gave diene 13. However, the yield went down as low as 18%.