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

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 w...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-11, Vol.127 (46), p.16038-16039
Main Authors: Coleman, Robert S, Walczak, Matthew C, Campbell, Erica L
Format: Article
Language:English
Subjects:
Antineoplastic agents
Biological and medical sciences
Cell Cycle - drug effects
Cells - chemistry
Cells - metabolism
Chemistry
Chemotherapy
Exact sciences and technology
Furans - chemical synthesis
Furans - chemistry
Furans - pharmacology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Medical sciences
Molecular Structure
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrroles - pharmacology
Tumor Suppressor Protein p53 - deficiency
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja056217g