One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides

2011/02/22 by Birgitta Pettersson, Vedran Hasimbegovic, Jan Bergman · 1 citation
Chemistry · #Advanced Synthetic Organic Chemistry #Chemical synthesis and alkaloids #Synthetic Organic Chemistry Methods

paper · doi:10.1021/jo101864n

openalex publication_date 2011/02/22 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02

Abstract

Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DMSO proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.

Citations

• Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d- and l-Glutamic Acid
• Macrocyclic lactone formation through sulfide contraction. Synthesis of (.+-.)-diplodialide A
• Sulfidkontraktion via alkylative Kupplung: Eine methode zur darstellung von β‐dicarbonylderivaten. Über synthetische methoden, 1. Mitteilung
• New approaches to the pyrrolizidine ring system: total synthesis of (.+-.)-isoretronecanol and (.+-.)-trachelanthamidine
• Recent advances in the chemistry of natural products

Cited by

• Eschenmoser sulfide contraction [wikipedia]

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