Prelog-Djerassi lactone, Carroll rearrangement

J. Rodriguez et al. have investigated the stereoselective ester dienolate Carroll rearrangement of ( )- and (Z)-allylic (3-keto esters and found a new, attractive approach to the synthesis of the Prelog-DJerassi lactone and related... 

Ouvrard, N., Rodriguez, J., Santelli, M. Stereoselective ester dienolate Carroll Rearrangement a New Approach to the Prelog-Djerassi lactone framework. Tetrahedron Lett. 1993, 34, 1149-1150. 

Using the Carroll rearrangement as the key step, Rodriguez and coworkers synthesized derivatives of the Prelog-Djerassi lactone (18) (Scheme 8.12) [16]. 

Rodriguez and co-workers envisioned the Carroll rearrangement as the key step in the preparation of the Prelog-Djerassi lactone 204. The dienolate of 200 conveniently rearranged via a chair-like transition state 201 to the y0-keto acid which underwent decarboxylation to give a 4 1 mixture of cyclopentanone epimers. Epimerization under thermodynamic conditions... 

---

See also in sourсe #XX -- [ , ]

---