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J Am Chem Soc. 2005 Nov 23;127(46):16038-9.

Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells.

Author information

1
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210-1185, USA. coleman@chemistry.ohio-state.edu

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.

PMID:
16287286
DOI:
10.1021/ja056217g
[Indexed for MEDLINE]
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