From Total Synthesis to Diverted Total Synthesis: Case Studies in the Amphidinolide Series

2011/03/24 by Alois Fürstner · 1 citation
Chemistry · Environmental Science · #Synthetic Organic Chemistry Methods #Catalytic Cross-Coupling Reactions #Marine Toxins and Detection Methods

paper · doi:10.1002/ijch.201100006

openalex publication_date 2011/03/24 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/22

Abstract

Abstract Amphidinolides are a class of structurally rather unique macrolides of marine origin which stimulated a lot of creative work in the total synthesis arena over the last decade. This review summarizes the strategies and tactics pursued by our group en route to various amphidinolides of the B, G, H, T, V, X, and Y series. These projects were invariably benefitting from the power of transition metal catalysis, with olefin and alkyne metathesis, palladium‐ and iron cross‐coupling, as well as asymmetric oxidation and reduction chemistry playing particularly prominent roles. Once the total syntheses were completed, the flexibility of the underlying blueprints enabled the extension of our program toward the preparation of non‐natural analogues for biological testing, all of which feature deep‐seated structural modifications in keeping with the logic of “diverted total synthesis”.

Citations

• Diverted total synthesis: Preparation of a focused library of latrunculin analogues and evaluation of their actin-binding properties
• A Rapid Esterification by Means of Mixed Anhydride and Its Application to Large-ring Lactonization
• The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]
• The Mechanisms of the Stille Reaction
• Large rate accelerations in the stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: mechanistic and synthetic implications
• The Development of L2X2RuCHR Olefin Metathesis Catalysts: An Organometallic Success Story
• The Effects of Harmful Algal Blooms on Aquatic Organisms
• Macrocyclization by Ring‐Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations
• A Stereoselective Synthesis oftrans-1,2-Disubstituted Alkenes Based on the Condensation of Aldehydes with Metallated 1-Phenyl-1H-tetrazol-5-yl Sulfones

Cited by

• Diverted total synthesis [wikipedia]