- Total synthesis of cryptophycin-24 (arenastatin A) via Prins cyclization
-
A stereoselective synthesis of fragment A of cryptophycin is achieved utilizing the versatile Prins cyclization. Subsequently, the total synthesis of cryptophycin-24 (arenastatin A) has been accomplished by coupling it with the depsipeptide subunit.
- Yadav,Purnima,Subba Reddy,Nagaiah,Ghamdi
-
p. 6709 - 6712
(2012/01/06)
-
- Stereoselective total synthesis of arenastatin A, a spongean cytotoxic depsipeptide
-
A highly stereoselective total synthesis of arenastatin A, an extremely potent cytotoxic cyclic depsipeptide from marine sponge, was developed. The desired 7,8-β-epoxide in arenastatin A was constructed by asymmetric sulfur ylide-mediated epoxidation in g
- Kotoku, Naoyuki,Narumi, Fuminori,Kato, Tomoya,Yamaguchi, Miho,Kobayashi, Motomasa
-
p. 7147 - 7150
(2008/03/11)
-
- Asymmetric syntheses of potent antitumor macrolides cryptophycin B and arenastatin A
-
Efficient and highly stereoselective syntheses of cryptophycin B and arenastatin A, potent cytotoxic agents, are described. An ester-derived titanium enolate mediated syn-aldol reaction was employed to generate the stereocenters C-5 and C-6. The route is convergent and provides a convenient access to the synthesis of structural variants of cryptophycins as well as members of its family. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
- Ghosh, Arun K.,Bischoff
-
p. 2131 - 2141
(2007/10/03)
-
- RCM approach for the total synthesis of cryptophycin-24 (Arenastatin A)
-
An efficient total synthesis of cryptophycin-24 (arenastatin A) is reported, which features two novel synthetic strategies, the use of a RCM reaction to form the macrocycle, and the introduction of the styrene epoxide moiety prior to the macrocyclization
- Tripathy, Narendra K.,Georg, Gunda I.
-
p. 5309 - 5311
(2007/10/03)
-
- Total synthesis and anti-tubulin activity of epi-C3 analogues of cryptophycin-24
-
Epi-C3-cryptophycin-24, epi-C3-m-chlorobenzyl-cryptophycin-24, and the corresponding styrenes were synthesized and tested in vitro against the MCF-7 and multidrug-resistant MCF-7/ADR breast cancer cell lines and in an in vitro tubulin assembly assay. The results demonstrate that the S configuration at the C3 stereocenter is not required to induce potent cytotoxicity and the m-Cl substituent present on the C10 side chain did not induce any large change in activity.
- Buck, Suzanne B.,Huff, Jacquelyn K.,Himes, Richard H.,Georg, Gunda I.
-
p. 3697 - 3699
(2007/10/03)
-
- Synthesis of Cryptophycins via an N-Acyl-β-lactam Macrolactonization
-
An efficient and concise approach to the synthesis of the macrolide core of the cryptophycins has been developed. A novel macrolactonization utilizing a reactive acyl-β-lactam intermediate incorporates the β-amino acid moiety within the 16-membered macrol
- Vidya, Ramdas,Eggen, MariJean,Nair, Sajiv K.,Georg, Gunda I.,Himes, Richard H.
-
p. 9687 - 9693
(2007/10/03)
-
- Rapid entry into the cryptophycin core via an acyl-beta-lactam macrolactonization: total synthesis of cryptophycin-24.
-
[see structure]. An efficient, concise approach to the macrolide core of the cryptophycins, potent antimitotic agents, has been achieved. The reaction sequence features a novel macrolactonization utilizing a reactive acyl-beta-lactam intermediate that inc
- Eggen,Nair,Georg
-
p. 1813 - 1815
(2007/10/03)
-
- Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide
-
In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A.
- Murakami, Nobutoshi,Tamura, Satoru,Wang, Weiqi,Takagi, Tatsuya,Kobayashi, Motomasa
-
p. 4323 - 4336
(2007/10/03)
-
- Total synthesis of cryptophycin-24 (arenastatin A) amenable to structural modifications in the C16 side chain
-
Two efficient protocols for the synthesis of tert-butyl (5S,6R,2E,7E)-5-[(tert-butyldimethylsilyl)-oxy]-6-methyl-8-phenyl-2,7-octadie noate, a major component of the cryptophycins, are reported. The first utilized the Noyori reduction and Frater alkylation of methyl 5-benzyloxy-3-oxopentanoate to set two stereogenic centers, which became the C16 hydroxyl and C1' methyl of the cryptophycins. The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-α-pinene to set both stereocenters in a single step and provided the dephenyl analogue, tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate, in five steps. This compound was readily converted to the 8-phenyl compound via Heck coupling. The silanyloxy esters were efficiently deprotected and coupled to the C2-C10 amino acid fragment to provide desepoxyarenastatin A and its dephenyl analogue. The terminal olefin of the latter was further elaborated via Heck coupling. Epoxidation provided cryptophycin-24 (arenastatin A).
- Eggen,Mossman,Buck,Nair,Bhat,Ali,Reiff,Boge,Georg
-
p. 7792 - 7799
(2007/10/03)
-
- Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae
-
A convergent synthesis of cryptophycins has been developed in which (5S,6R)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic acid (A) is coupled with an amino acid segment (B). Two stereo-selective routes to A are described, the first employing allylatio
- White, James D.,Hong, Jian,Robarge, Lonnie A.
-
p. 6206 - 6216
(2007/10/03)
-
- A concise synthesis of the cytotoxic depsipeptide arenastatin A
-
Arenastatin A (1, cryptophycin 24) was synthesized by convergence of hydroxy ester 16 with amino acid derivative 27; two independent and highly efficient routes to 16 are disclosed.
- White, James D.,Hong, Jian,Robarge, Lonnie A.
-
p. 8779 - 8782
(2007/10/03)
-
- A total synthesis of arenastatin A, an extremely potent cytotoxic depsipeptide, from the Okinawan marine sponge dysidea arenaria
-
An asymmetric synthesis of a cyclic depsipeptide arenastatin A (1), which was isolated from the marine sponge Dysidea arenaria and exhibited extremely potent cytotoxicity with IC50 5 pg/ml for KB cells, has been accomplished.
- Kobayashi,Kurosu,Wang,Kitagawa
-
p. 2394 - 2396
(2007/10/02)
-