Get 20M+ Full-Text Papers For Less Than $1.50/day. Start a 14-Day Trial for You or Your Team.

Learn More →

A Modular Synthesis of Antitumor Macrolide (–)‐Lasonolide A†

A Modular Synthesis of Antitumor Macrolide (–)‐Lasonolide A† Lasonolide A was identified as a potent antitumor macrolide towards various cancer cell lines. The two tetrahydropyrans bearing multiple stereogenic centers as well as the polyene linkage attracted a dozen synthetic research groups to launch the total synthesis. Based on the synthetic methods developed in our group, namely, the hydroboration of allene and its subsequent allylation as well as the iterative hydroboration of allene and oxidation, the polyol subunits were efficiently constructed and then integrated into the final target. A new Julia olefination reagent, double‐headed sulfone, was designed to promote the rapid coupling of two aldehydes bearing multiple functional groups to secure the whole carbon framework. Another highlight of our approach is the application of a traceless protecting group, 9‐BBN (9‐borabicyclo[3.3.1]nonane), to hide the secondary alcohol for debenzylation, and for the first time, to mask the carboxylic acid for Julia olefination under strong basic conditions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chinese Journal of Chemistry Wiley

A Modular Synthesis of Antitumor Macrolide (–)‐Lasonolide A†

Loading next page...
 
/lp/wiley/a-modular-synthesis-of-antitumor-macrolide-lasonolide-a-Fhn0JHv3vy

References (75)

Publisher
Wiley
Copyright
© 2020 SIOC, CAS, Shanghai, & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
1001-604X
eISSN
1614-7065
DOI
10.1002/cjoc.202000026
Publisher site
See Article on Publisher Site

Abstract

Lasonolide A was identified as a potent antitumor macrolide towards various cancer cell lines. The two tetrahydropyrans bearing multiple stereogenic centers as well as the polyene linkage attracted a dozen synthetic research groups to launch the total synthesis. Based on the synthetic methods developed in our group, namely, the hydroboration of allene and its subsequent allylation as well as the iterative hydroboration of allene and oxidation, the polyol subunits were efficiently constructed and then integrated into the final target. A new Julia olefination reagent, double‐headed sulfone, was designed to promote the rapid coupling of two aldehydes bearing multiple functional groups to secure the whole carbon framework. Another highlight of our approach is the application of a traceless protecting group, 9‐BBN (9‐borabicyclo[3.3.1]nonane), to hide the secondary alcohol for debenzylation, and for the first time, to mask the carboxylic acid for Julia olefination under strong basic conditions.

Journal

Chinese Journal of ChemistryWiley

Published: Jul 1, 2020

Keywords: ; ; ; ;

There are no references for this article.