Use of allylic strain to enforce stereochemistry. Direct syntheses of 7,8-dihydroxycalamenene and mansonone C.
[Structure: see text] Direct syntheses of 7,8-dihydroxycalamenene and mansonone C were achieved. The cis-stereochemistry required for the synthesis of 7,8-dihydroxycalamenene was introduced by an intramolecular cyclization directed by allylic strain.
Kraus
George A
GA
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA. gakraus@iastate.edu
Jeon
Insik
I
D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis*; D013729:Terpenes / Q000138:chemical synthesis*; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis*
C517071:7,8-dihydroxycalamenene; D009285:Naphthoquinones; D013729:Terpenes; D013764:Tetrahydronaphthalenes; C517072:mansonone C