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Literature DB >> 33794050

Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol-Mediated syn- and anti-Diastereoselective Carbonyl Crotylation.

Abstract

The potent spliceosome modulator pladienolide B, which bears 10 stereogenic centers, is prepared in 10 steps (LLS). Asymmetric alcohol-mediated carbonyl crotylations catalyzed by ruthenium and iridium that occur with syn- and anti-diastereoselectivity, respectively, were used to form the C20-C21 and C10-C11 C-C bonds.

Entities: Chemical

Keywords: cancer; enantioselective; hydrogen transfer; iridium; ruthenium

Mesh：

Substances：

Year: 2021 PMID： 33794050 PMCID： PMC8190871 DOI： 10.1002/anie.202103845

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 16.823

36 in total

1. Total synthesis of the potent antitumor macrolides pladienolide B and D.

Authors: Regina M Kanada; Daisuke Itoh; Mitsuo Nagai; Jun Niijima; Naoki Asai; Yoshiharu Mizui; Shinya Abe; Yoshihiko Kotake
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Total Synthesis of Amphirionin-4.

Authors: Yusuke Ogura; Hikaru Sato; Shigefumi Kuwahara
Journal: Org Lett Date: 2016-04-12 Impact factor: 6.005

3. Synthesis of a pladienolide B analogue with the fully functionalized core structure.

Authors: Sarah Müller; Timo Mayer; Florenz Sasse; Martin E Maier
Journal: Org Lett Date: 2011-06-27 Impact factor: 6.005

4. Enhanced anti-diastereo- and enantioselectivity in alcohol-mediated carbonyl crotylation using an isolable single component iridium catalyst.

Authors: Xin Gao; Ian A Townsend; Michael J Krische
Journal: J Org Chem Date: 2011-03-04 Impact factor: 4.354

5. Total synthesis of 6-deoxypladienolide D and Assessment of Splicing Inhibitory Activity in a Mutant SF3B1 cancer cell line.

Authors: Kenzo Arai; Silvia Buonamici; Betty Chan; Laura Corson; Atsushi Endo; Baudouin Gerard; Ming-Hong Hao; Craig Karr; Kazunobu Kira; Linda Lee; Xiang Liu; Jason T Lowe; Tuoping Luo; Lisa A Marcaurelle; Yoshiharu Mizui; Marta Nevalainen; Morgan Welzel O'Shea; Eun Sun Park; Samantha A Perino; Sudeep Prajapati; Mingde Shan; Peter G Smith; Parcharee Tivitmahaisoon; John Yuan Wang; Markus Warmuth; Kuo-Ming Wu; Lihua Yu; Huiming Zhang; Guo-Zhu Zheng; Gregg F Keaney
Journal: Org Lett Date: 2014-10-26 Impact factor: 6.005

6. Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors: Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal: Acc Chem Res Date: 2017-08-09 Impact factor: 22.384

Review 7. Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors: Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal: Nat Prod Rep Date: 2014-02-11 Impact factor: 13.423

8. Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. III. In vitro and in vivo antitumor activities.

Authors: Yoshiharu Mizui; Takashi Sakai; Masao Iwata; Toshimitsu Uenaka; Kiyoshi Okamoto; Hajime Shimizu; Takao Yamori; Kentaro Yoshimatsu; Makoto Asada
Journal: J Antibiot (Tokyo) Date: 2004-03 Impact factor: 2.649