title: Stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3.
abstract: A stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3 has been described. The synthesis is completed in 7 steps with 10.5% and 13% overall yields for (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L respectively. The key steps involve Dötz benzannulation of carbene 5 with alkyne 6 to give a substituted naphthalene moiety and oxa-Pictet-Spengler reaction to install the 1,3-dimethylpyran moiety.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, Maharashtra, India. rfernand@chem.iitb.ac.in
authors.forename: Rodney A
authors.initials: RA
authors.lastname: Fernandes
authors.forename: Arun B
authors.initials: AB
authors.lastname: Ingle
authors.forename: Vijay P
authors.initials: VP
authors.lastname: Chavan
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis*; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D016227:Benzoquinones; D009285:Naphthoquinones; D011714:Pyrans; C523641:cardinalin 3; C501541:ventiloquinone L