A convenient synthesis of a-ring-functionalized podolactones. Revision of the structure of wentilactone B.

Alejandro F Barrero, María M Herrador, José F Quílez del Moral, Mónica V Valdivia

Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuentenueva, 18071 Granada, Spain. afbarre@goliat.ugr.es

Organic letters 2002 Apr 18

filter terms:

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]

Citation

Alejandro F Barrero, María M Herrador, José F Quílez del Moral, Mónica V Valdivia. A convenient synthesis of a-ring-functionalized podolactones. Revision of the structure of wentilactone B. Organic letters. 2002 Apr 18;4(8):1379-82