Sign in to use this feature.

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline
remove_circle_outline

Journals

Article Types

Countries / Regions

Search Results (2)

Search Parameters:
Keywords = Matteson homologation

Order results
Result details
Results per page
Select all
Export citation of selected articles as:
39 pages, 14151 KiB  
Review
Syntheses of Marine Natural Products via Matteson Homologations and Related Processes
by Uli Kazmaier
Mar. Drugs 2025, 23(1), 20; https://doi.org/10.3390/md23010020 - 2 Jan 2025
Cited by 3 | Viewed by 2608
Abstract
Matteson homologation, a successive extension of chiral boronic esters, is perfectly suited for the synthesis of complex molecular structures containing several stereogenic centers. The “classical version” allows the introduction of various functional groups in a 1,2-anti-configuration. The absolute configuration is determined [...] Read more.
Matteson homologation, a successive extension of chiral boronic esters, is perfectly suited for the synthesis of complex molecular structures containing several stereogenic centers. The “classical version” allows the introduction of various functional groups in a 1,2-anti-configuration. The absolute configuration is determined by the choice of the chiral auxiliary, which can be used to introduce several stereogenic centers. In contrast, in Aggarwal’s lithiation-borylation strategy, new chiral auxiliary reagents must be used in each reaction step, which on the other hand allows the individual insertion of the desired stereogenic centers. Both methods have their individual advantages and disadvantages and are well suited for the synthesis of marine natural products. Full article
Show Figures

Figure 1

24 pages, 1549 KiB  
Article
Synthesis and Late-Stage Modification of (−)-Doliculide Derivatives Using Matteson’s Homologation Approach
by Markus Tost and Uli Kazmaier
Mar. Drugs 2024, 22(4), 165; https://doi.org/10.3390/md22040165 - 8 Apr 2024
Cited by 4 | Viewed by 2194
Abstract
(−)-Doliculide, a marine cyclodepsipeptide derived from the Japanese sea hare, Dolabella auricularia, exhibits potent cytotoxic properties, sparking interest in the field of synthetic chemistry. It is comprised of a peptide segment and a polyketide moiety, rendering it amenable to Matteson’s homologation methodology. [...] Read more.
(−)-Doliculide, a marine cyclodepsipeptide derived from the Japanese sea hare, Dolabella auricularia, exhibits potent cytotoxic properties, sparking interest in the field of synthetic chemistry. It is comprised of a peptide segment and a polyketide moiety, rendering it amenable to Matteson’s homologation methodology. This technique facilitates the diversification of the distinctive polyketide side chain, thereby permitting the introduction of functional groups in late stages for modifications of the derived compounds and studies on structure–activity relationships. Full article
(This article belongs to the Special Issue Marine Bioactive Peptides—Structure, Function, and Application 2.0)
Show Figures

Graphical abstract

Back to TopTop