
TY  - JOUR
A1  - Macleod, JK 
A1  - Morris, KB 
T1  - Synthetic Studies on Wedeligenin: Preparation of an A/B-Ring Intermediate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1995
VL  - 48
IS  - 3
SP  - 609
EP  - 624
KW  - 
UR  - https://doi.org/10.1071/CH9950609 
N2  - In a new approach to the synthesis of wedeligenin , an A/B-ring intermediate (13a) has been synthesized. The &#946;- keto ester (15) was readily prepared from Wieland-Meischer  ketone in three steps. Baeyer-Villiger oxidation of (15) and subsequent methylenation provided an alkene (16) which contained the malonyl substituent, later to become the gem-diester of (13a). Regiospecific conversion of the alkene into a bromohydrin followed by cyclization afforded (13a). This provided an A/B-ring intermediate which could be further elaborated to allow C/D-ring annulation. 
ER  -

