Identification and Synthesis of New γ-Lactones from Tuberose Absolute (Polianthes tuberosa)

Article abstract of DOI:10.1002/hlca.19820650204

Six unsaturated γ-lactones, (Z)-5-octen-4-olide (1), (Z)-5-decen-4-olide (2), (Z)-6-nonen-4-olide (3), (Z)-6-dodecen-4-olide (4), (Z,Z)-6,9-dodecadien-4-olide (5), and tuberolide (6) have been identified for the first time in tuberose absolute (from Polianthes tuberosa L.).All structures were corroborated by synthesis and all, except 3 and 4, are new.An improved method for the stereoselective synthesis of (+/-)-cis-bicyclo<4.3.>-non-3-en-7-one (23) by an AlCl3-catalyzed Diels-Alder reaction is reported.