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Synlett 1991; 1991(11): 789-791
DOI: 10.1055/s-1991-20876
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First Synthetic Approach to Spongian Pentacyclic Diterpenoids. Enantioselective Synthesis of Dendrillol-1

Antonio Abad* , Manuel Arnó, M. Luisa Marín, Ramón J. Zaragozá
  • *Departamento de Química Orgínica, Facultad de Químicas, Universitad de Valencia, Dr. Moliner 50, E-46100 Burjassot, Valencia, Spain
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Publication Date:
07 March 2002 (online)

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The enantioselective synthesis of the spongian diterpene dendrillol-1 (3), from chiral (+)-podocarp-8(14)-en-13-one (5) of known absolute configuration, is described. Key intermediate in this synthesis is the acid-dialdehyde 4 (8,14-diformylpodocarpane-13-carboxylic acid), which was prepared from 5 by a reaction sequence involving photo-addition of acetylene, nucleophilic carboxylation, reductive dehydroxylation, and ozonolysis.