73397-35-0Relevant academic research and scientific papers
β-lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids
Wasserman, Harry H,Matsuyama, Haruo,Robinson, Ralph P
, p. 7177 - 7190 (2007/10/03)
Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine (1) and (±)-dihydroperiphylline (2) as well as the related spermine alkaloid (±)-verbascenine (3) were accomplished by means of sequential ring expansions of smaller lactam rings. Three ring expansion methods were employed: (1) transamidation of N-(aminoalkyl)lactams, (2) β-lactam-lactim ether condensation followed by reductive cleavage of the bicyclic 4-oxotetrahydropyrimidine product with NaBH3CN/AcOH and (3) bicyclic acyl hydrazine formation followed by N-N bond cleavage with Na/NH3. Each synthesis features ring expansion of a 4-phenylazetidin-2-one intermediate that undergoes transamidative ring expansion or lactim ether condensation.
Lithium and proton templated ω-polyazamacrolactamization, new general routes to macrocyclic polyamines
Drandarov, Konstantin,Hesse, Manfred
, p. 7213 - 7216 (2007/10/03)
A general, lithium templated/catalyzed ω-polyazamacrolactamization method for the synthesis of macrocyclic polyamines including spermidine and spermine alkaloids is presented. The formation of 12-, 13-, 16-, 17-, and 19-membered N3, N4, N5, and N6 containing rings is described. A proton templated/catalyzed macrolactamization of some ω-polyazaaminoesters is also observed.
SYNTHESIS OF THE SPERMIDINE ALKALOID (+/-)-N(1)-ACETYL-N(1)-DEOXYMAYFOLINE
Tawil, Bassim F.,Guggisberg, Armin,Hesse, Manfred
, p. 3775 - 3780 (2007/10/02)
The total synthesis of the spermidine alkaloid (+/-)-N(1)-acetyl-N(1)-deoxymayfoline ((+/-)-1) was achieved by expansion of rings.The 5-membered cyclic compound 2 was fused with butadiene by intermolecular Diels-Alder cycloaddition.The resulting 7-phenyl-
NEW APPROACHES TO THE SYNTHESIS OF SPERMINE AND SPERMIDINE ALKALOIDS
Wasserman, Harry H.,Robinson, Ralph P.
, p. 279 - 288 (2007/10/02)
New approaches to the formation of macrocyclic lactams are described involving successive ring expansion of 8-lactams and other heterocyclic systems.These methods have been used in the synthesis of a number of spermine and spermidine alkaloids including homaline, celacinnine, dihydroperiphylline, chaenorhine and verbascenine.
Total Synthesis of (+/-)-Celacinnine, (+/-)-Celallocinnine, (+/-)-Celafurine, and (+/-)-Celabenzine
Yamamoto, Hisashi,Maruoka, Keiji
, p. 6133 - 6136 (2007/10/02)
The total synthesis of spermidine alkaloids, (+/-)-celacinnine (2), (+/-)-celallocinnine (3), (+/-)-celafurine (4), and (+/-)-celabenzine (5), is described.The use of boron-templated cyclization within the context of constructing macrolactam has been explored, and the combination of triamino ester with tris(dimethylamino)borane is found to be highly efficient.The present cyclization in addition to the refinement of each step produces macrocyclic spermidine alkaloids, 2, 4, and 5, by a five-step sequence in ca. 41percent overall yield starting from 1,4-diaminobutane.Irradiation of 2 affords 3 in 50percent yield.
Chemistry of Naturally Occuring Polyamines. 1. Total Synthesis of Celacinnine, Celabenzine, and Maytenine
McManis, James S.,Ganem, Bruce
, p. 2041 - 2042 (2007/10/02)
New methods for the selective functionalization of spermidine and other naturally occurring polyamines have been employed in highly convergent total syntheses of the title compounds.
TRANSAMIDATION REACTIONS IN THE FORMATION OF MACROCYCLIC LACTAMS. A TOTAL SYNTHESIS OF CELLACINNINE.
Wasserman, Harry H.,Robinson, Ralph P.,Matsuyama, Haruo
, p. 3493 - 3496 (2007/10/02)
The macrocyclic spermidine alkaloid, cellacinnine, has been synthetized by methods involving successive ring expansion reactions.One route starts with 4-phenyl-2-azetidinone; another, with piperidazine.
