Chemistry of renieramycins. Part 11: Total synthesis of (±)-cribrostatin 4

Autor: Naoki Saito, Hiroshi Ito, Masashi Yokoya

Publikováno v: Tetrahedron. 67:9185-9192

A 19-step synthesis of (±)-cribrostatin 4 ( 1 ) from readily available piperazine-2,5-dione derivative 6 is described. The synthesis features the concise construction of a pentacyclic framework, followed by the base-catalyzed epimerization of the C-

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::bedd1d7b1f5f5ae63ae5657b7a662d86
https://doi.org/10.1016/j.tet.2011.09.076

ChemInform Abstract: Synthesis of Renieramycins: Construction of the Core Ring System of Cribrostatin 4 Through Modified Pictet-Spengler Cyclization of 3,6-Bisarylpiperazine-2,5-dione with Diethoxyethyl Benzoate

Autor: Hiroshi Ito, Naoki Saito, Masashi Yokoya

Publikováno v: ChemInform. 42

The synthesis of the compound (V), which is a key intermediate in the synthesis of cribrostatin 4 can be achieved by a stereoselective cyclization, cf.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::75b414e5f331474c1a2ade44a1574e45
https://doi.org/10.1002/chin.201149193

ChemInform Abstract: Synthesis of Tetrahydroisoquinoline Antitumor Natural Products: Construction of Tricyclic Lactams Through Pictet-Spengler-Type Cyclization of N-Methyl-3-arylmethylpiperazine-2,5-dione with Ethyl Diethoxyacetate

Autor: Naoki Saito, Masashi Yokoya, Osamu Kawachi

Publikováno v: ChemInform. 40

6-Hydroxymethyl-7,8,10-trimethoxy-2,6-dimethyl-3,6,11,11a-tetrahydro-2H-pyrazino[1,2-b]isoquinoline-1,4-dione (10) was prepared stereoselectively by Pictet-Spengler-type cyclization of the O,N-acetal of 3-arylmethylpiperazine-2,5-dione (8) in high yi

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::c6bc2beee1a7518af1f374e73ede7077
https://doi.org/10.1002/chin.200918159

Total Synthesis of the Marine Natural Product (-)-Cribrostatin 4 (Renieramycin H)

Autor: Xiaochuan Chen, Jieping Zhu

Publikováno v: Angewandte Chemie International Edition
Angewandte Chemie International Edition, Wiley-VCH Verlag, 2007, 46 (21), pp.3962-3965. ⟨10.1002/anie.200700539⟩

The cytotoxic title compd. (-)-cribrostatin 4 (I) was synthesized from five readily available starting materials in a longest linear sequence of 21 steps and 4.3% overall yield. The key step in the construction of the pentacyclic core of I was a domi

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b3faa628ce74abeac871187bb35f50b2
https://doi.org/10.1002/chin.200736192

Corrigendum: Asymmetric Total Synthesis of (−)-Cribrostatin 4 (Renieramycin H)

Autor: Robert M. Williams, Guillaume Vincent

Publikováno v: Angewandte Chemie International Edition. 50:8458-8458

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::ebee5763e2086f77f7cf071715b29cad
https://doi.org/10.1002/anie.201190074