Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester

An enantioselective total synthesis of spliceostatin G has been accomplished. The synthesis involved a Suzuki cross-coupling reaction as a key step. The functionalized tetrahydropyran ring was constructed from commercially available optically active tri-O-acetyl-d-glucal. Other key reactions include...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2018-01, Vol.20 (1), p.96-99
Main Authors: Ghosh, Arun K, Reddy, Guddeti Chandrashekar, MacRae, Andrew J, Jurica, Melissa S
Format: Article
Language:English
Subjects:
Amination
Esters - chemistry
Molecular Structure
RNA Splicing
Spiro Compounds
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An enantioselective total synthesis of spliceostatin G has been accomplished. The synthesis involved a Suzuki cross-coupling reaction as a key step. The functionalized tetrahydropyran ring was constructed from commercially available optically active tri-O-acetyl-d-glucal. Other key reactions include a highly stereoselective Claisen rearrangement, a Cu­(I)-mediated 1,4 addition of MeLi to install the C8 methyl group, and a reductive amination to incorporate the C10 amine functionality of spliceostatin G. Biological evaluation of synthetic spliceostatin G and its methyl ester revealed that it does not inhibit splicing in vitro.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03456