A convenient synthesis of a-ring-functionalized podolactones. Revision of the structure of wentilactone B.
A new route to podolactones functionalized in the A ring has been achieved. Two key steps were employed in this synthesis, the construction of the bicyclic skeleton via a Mn(III)-mediated radical cyclization and the transformation of this bicyclic intermediate into the tetracyclic podolactone skeleton through a Pd (II)-mediated bislactonization of the corresponding conjugate diene. The reported synthesis of 3beta-hydroxy-13,14,15,16-tetranorlabda-7,9(11)-dien-(19,6beta),(12,17)-diolide (1) let us reassign the structure of wentilactone B, for which structure 1 was wrongly reported. [reaction: see text]
Barrero
Alejandro F
AF
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuentenueva, 18071 Granada, Spain. afbarre@goliat.ugr.es
Herrador
María M
MM
Quílez del Moral
José F
JF
Valdivia
Mónica V
MV
D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry*; D013729:Terpenes / Q000138:chemical synthesis*
D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D007783:Lactones; D013729:Terpenes; C454809:wentilactone B