Total Synthesis of Iejimalide B. An Application of the Shiina Macrolactonization

2007/10/01 by Dirk Schweitzer, John J. Kane, Daniel Strand +3 · 2 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Synthetic Organic Chemistry Methods #Marine Sponges and Natural Products #Oxidative Organic Chemistry Reactions

paper · doi:10.1021/ol702129w

openalex publication_date 2007/10/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

The potent anticancer compound iejimalide B (1) was prepared by a total synthesis through a strategy that features Julia olefinations, Wittig olefinations, a Carreira enantioselective alkynylation, a Heck reaction, a Marshall propargylation reaction, a Stille coupling, and a Shiina macrolactonization.

Citations

• The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
• Syntheses a l'aide de sulfones v(+)- methode de synthese generale de doubles liaisons.
• A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2′-alkenyl)- or benzyl-sulfonyl]-benzothiazoles.

Cited by

• 2-Methyl-6-nitrobenzoic Anhydride (MNBA)
• 2-Methyl-6-nitrobenzoic anhydride [wikipedia]