Literature DB >> 25110364

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

Ashutosh Pal1, Zhenghong Peng1, Paul T Schuber1, Basvoju A Bhanu Prasad1, William G Bornmann1.   

Abstract

The C1-C6 region of the potent cytotoxic agent psymberin has been synthesized. The key transformations of the synthesis are an auxiliary-controlled addition of a Sn(II)-glycolate enolate to an aldehyde to yield the anti aldol product and transforming the primary alcohol into a terminal olefin utilizing organoselenium chemistry.

Entities:  

Year:  2013        PMID： 25110364      PMCID： PMC4124943          DOI： 10.1016/j.tetlet.2013.05.153

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

1.  Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors:  Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

2.  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

Review 3.  Isolation, biological activity, synthesis, and medicinal chemistry of the pederin/mycalamide family of natural products.

Authors:  R Adam Mosey; Paul E Floreancig
Journal:  Nat Prod Rep       Date:  2012-07-09       Impact factor: 13.423

4.  Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products.

Authors:  Xin Jiang; Noelle Williams; Jef K De Brabander
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

5.  Synthesis and confirmation of the absolute stereochemistry of the (-)-aflastatin A C9-C27 degradation polyol.

Authors:  David A Evans; William C Trenkle; Jing Zhang; Jason D Burch
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

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

Authors:  Tsubasa Watanabe; Takamichi Imaizumi; Takumi Chinen; Yoko Nagumo; Masatoshi Shibuya; Takeo Usui; Naoki Kanoh; Yoshiharu Iwabuchi
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

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

Authors:  Chihui An; Adam T Hoye; Amos B Smith
Journal:  Org Lett       Date:  2012-08-14       Impact factor: 6.005

Review 8.  Exploring the chemistry of uncultivated bacterial symbionts: antitumor polyketides of the pederin family.

Authors:  Jörn Piel; Daniel Butzke; Nobuhiro Fusetani; Dequan Hui; Matthias Platzer; Gaiping Wen; Shigeki Matsunaga
Journal:  J Nat Prod       Date:  2005-03       Impact factor: 4.050

9.  The total synthesis of psymberin.

Authors:  Xianhai Huang; Ning Shao; Anandan Palani; Robert Aslanian; Alexei Buevich
Journal:  Org Lett       Date:  2007-05-25       Impact factor: 6.005

10.  Studies toward the unique pederin family member psymberin: structure-activity relationships, biochemical studies, and genetics identify the mode-of-action of psymberin.

Authors:  Cheng-Yang Wu; Yu Feng; Eduardo R Cardenas; Noelle Williams; Paul E Floreancig; Jef K De Brabander; Michael G Roth
Journal:  J Am Chem Soc       Date:  2012-11-13       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.