ASYMMETRIC TOTAL SYNTHESIS OF STOECHOSPERMOL USING INTRAMOLECULAR (2+2) PHOTOCYCLOADDITION REACTION

Article abstract of DOI:10.1016/S0040-4039(00)98611-8

The first asymmetric total synthesis of stoechospermol, a representative spatane diterpene having cis, anti, cis-tricyclo<5.3.0.0^2,6>decane ring system, was achieved.Using the intramolecular asymmetric (2+2) photocycloaddition reaction of the diastereomeric ester 11, the readily available butenolide 9 was transformed into the optically active dilactone 12a and 12b.Subsequent construction of tricyclic carbon ring system and introduction of substituents in a right stereochemistry gave rise to optically pure stoechospermol 1.