Unknown

Dataset Information

0

Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome.


ABSTRACT: Enantioselective syntheses of FR901464 and spliceostatin A, potent spliceosome inhibitors, are described. The synthesis of FR901464 has been accomplished in a convergent manner in 10 linear steps (20 total steps). The A-tetrahydropyran ring was constructed from (R)-isopropylidene glyceraldehyde. The functionalized tetrahydropyran B-ring was synthesized utilizing a Corey-Bakshi-Shibata reduction, an Achmatowicz reaction, and a stereoselective Michael addition as the key steps. Coupling of A- and B-ring fragments was accomplished via cross-metathesis.

SUBMITTER: Ghosh AK 

PROVIDER: S-EPMC3827971 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

altmetric image

Publications

Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome.

Ghosh Arun K AK   Chen Zhi-Hua ZH  

Organic letters 20130919 19


Enantioselective syntheses of FR901464 and spliceostatin A, potent spliceosome inhibitors, are described. The synthesis of FR901464 has been accomplished in a convergent manner in 10 linear steps (20 total steps). The A-tetrahydropyran ring was constructed from (R)-isopropylidene glyceraldehyde. The functionalized tetrahydropyran B-ring was synthesized utilizing a Corey-Bakshi-Shibata reduction, an Achmatowicz reaction, and a stereoselective Michael addition as the key steps. Coupling of A- and  ...[more]

Similar Datasets

| S-EPMC4066912 | biostudies-literature
| S-EPMC3482479 | biostudies-literature
| S-EPMC2965229 | biostudies-literature
| S-EPMC5972028 | biostudies-literature
| S-EPMC4260646 | biostudies-literature
| S-EPMC8512135 | biostudies-literature
| S-EPMC2530894 | biostudies-literature
| S-EPMC3482464 | biostudies-literature
| S-EPMC6519444 | biostudies-literature
| S-EPMC6594018 | biostudies-literature