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Literature DB >> 22892009

Total synthesis of (-)-irciniastatin B and structural confirmation via chemical conversion to (+)-irciniastatin A (psymberin).

Abstract

The total synthesis and structural confirmation of the marine sponge cytotoxin (-)-irciniastatin B has been achieved via a unified strategy employing a late-stage, selective deprotection/oxidation sequence that provides access to both (+)-irciniastatin A (psymberin) and (-)-irciniastatin B.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2012 PMID： 22892009 PMCID： PMC3438514 DOI： 10.1021/ol301783p

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

12 in total

1. Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa.

Authors: George R Pettit; Jun-Ping Xu; Jean-Charles Chapuis; Robin K Pettit; Larry P Tackett; Dennis L Doubek; John N A Hooper; Jean M Schmidt
Journal: J Med Chem Date: 2004-02-26 Impact factor: 7.446

2. Total Synthesis of (+)-Papulacandin D.

Authors: Scott E Denmark; Tetsuya Kobayashi; Christopher S Regens
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

3. Irciniastatin A induces JNK activation that is involved in caspase-8-dependent apoptosis via the mitochondrial pathway.

Authors: Takumi Chinen; Yoko Nagumo; Tsubasa Watanabe; Takamichi Imaizumi; Masatoshi Shibuya; Takao Kataoka; Naoki Kanoh; Yoshiharu Iwabuchi; Takeo Usui
Journal: Toxicol Lett Date: 2010-12-15 Impact factor: 4.372

4. The discovery of potent antitumor agent C11-deoxypsymberin/irciniastatin A: total synthesis and biology of advanced psymberin analogs.

Authors: Xianhai Huang; Ning Shao; Robert Huryk; Anandan Palani; Robert Aslanian; Cynthia Seidel-Dugan
Journal: Org Lett Date: 2009-02-19 Impact factor: 6.005

5. Total synthesis and biological evaluation of pederin, psymberin, and highly potent analogs.

Authors: Shuangyi Wan; Fanghui Wu; Jason C Rech; Michael E Green; Raghavan Balachandran; W Seth Horne; Billy W Day; Paul E Floreancig
Journal: J Am Chem Soc Date: 2011-09-22 Impact factor: 15.419

6. Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: total synthesis of psymberin.

Authors: Seong Rim Byeon; Heekwang Park; Hyoungsu Kim; Jiyong Hong
Journal: Org Lett Date: 2011-10-11 Impact factor: 6.005

3. Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents.

Authors: Qi Liu; Chihui An; Karen TenDyke; Hongsheng Cheng; Young Yongchun Shen; Adam T Hoye; Amos B Smith
Journal: J Org Chem Date: 2016-02-16 Impact factor: 4.354

3 in total

Total synthesis of (-)-irciniastatin B and structural confirmation via chemical conversion to (+)-irciniastatin A (psymberin).

1. Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa.

2. Total Synthesis of (+)-Papulacandin D.

3. Irciniastatin A induces JNK activation that is involved in caspase-8-dependent apoptosis via the mitochondrial pathway.

4. The discovery of potent antitumor agent C11-deoxypsymberin/irciniastatin A: total synthesis and biology of advanced psymberin analogs.

5. Total synthesis and biological evaluation of pederin, psymberin, and highly potent analogs.

6. Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: total synthesis of psymberin.

7. Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue.

8. Total synthesis of (+)-psymberin (irciniastatin A): catalytic reagent control as the strategic cornerstone.

9. Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy.

10. The total synthesis of psymberin.

1. Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

2. Total synthesis of (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin B.

3. Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents.