Article ; Online: Stereodivergent Total Syntheses of (+)-Mycaperoxides C, D, G Methyl Ester and (-)-Mycaperoxide B.
Chemistry (Weinheim an der Bergstrasse, Germany)
2022 Volume 29, Issue 6, Page(s) e202203004
Abstract: ... the total syntheses of (+)-mycaperoxides D, C, G methyl ester, and (-)-mycaperoxide B in 11 to 15 steps ... toward (+)-mycaperoxide D methyl ester (2), the isolation of the eight possible diastereomers under their ethyl thioester ...
Abstract | Mycaperoxides are natural endoperoxides isolated from different Mycale genus sponges, showing significant antiviral or antibacterial activities. We report herein the first total syntheses of representative congeners of this family from sclareol using a stereodivergent approach. Thus, an innovative oxidative ring expansion of cyclobutanol was used to bring the 1,2-dioxane subunit, and a Mukaiyama aldol reaction on peroxycarbenium species was utilized to install the propionic acid subunit. During the study toward (+)-mycaperoxide D methyl ester (2), the isolation of the eight possible diastereomers under their ethyl thioester form allowed to build a pertinent database for further NMR assignment studies. Thus, we completed the total syntheses of (+)-mycaperoxides D, C, G methyl ester, and (-)-mycaperoxide B in 11 to 15 steps, confirming their original assignment. |
---|---|
MeSH term(s) | Esters ; Magnetic Resonance Spectroscopy ; Stereoisomerism |
Chemical Substances | Esters |
Language | English |
Publishing date | 2022-12-07 |
Publishing country | Germany |
Document type | Journal Article |
ZDB-ID | 1478547-X |
ISSN | 1521-3765 ; 0947-6539 |
ISSN (online) | 1521-3765 |
ISSN | 0947-6539 |
DOI | 10.1002/chem.202203004 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
Full text online
More links
Kategorien
Order via subito
This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.