Concise, regioselective synthesis of the ABC tristetrahydropyran of thyrsiferol and venustatriol.
[structure: see text] The ABC tristetrahydropyran substructure 1 of the natural products thyrsiferol (2) and venustatriol (3) has been synthesized in 14 steps from farnesyl acetate, with effective control of all aspects of regio- and stereoselectivity in the formation of each tetrahydropyran ring.
McDonald
Frank E
FE
Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322, USA. fmcdona@emory.edu
Wei
Xudong
X
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D000461:Rhodophyta / Q000737:chemistry*
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D005663:Furans; D007202:Indicators and Reagents; D011714:Pyrans; C410453:venustatriol; C410452:thyrsiferol