Total Synthesis of Lucilactaene, A Cell Cycle Inhibitor Active in p53-Inactive Cells

2005/10/27 by Robert S. Coleman, Matthew C. Walczak, Erica Campbell · 2 citations
Medicine · Chemistry · #Cancer-related Molecular Pathways #Synthetic Organic Chemistry Methods #Synthesis of Organic Compounds

paper · doi:10.1021/ja056217g

openalex publication_date 2005/10/27 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.

Citations

• The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]
• A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium
• New perspectives in the cross-coupling reactions of organostannanes
• Palladium-Catalysed Reactions of Organotin Compounds

Cited by

• Asymmetric α-selective allylation of the amide unit of maleimides and alkenyloxindoles by dual-functional In III / N , N ′-dioxide complex
• Stille reaction [wikipedia]