918872-27-2Relevant academic research and scientific papers
Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone
Sharma, Gangavaram V.M.,Mallesham, Samala
experimental part, p. 2646 - 2658 (2011/02/16)
The total synthesis of (+)-crassalactone B, (+)-crassalactone C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone, and (+)-dicinnamoyl goniofufurone is achieved by a 'chiron approach' starting from diacetone d-glucose (DAG). Mitsunobu inversion, Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate. Meldrum's acid was used for the synthesis of (+)-crassalactone C, (+)-goniofufurone, and (+)-dicinnamoyl goniofufurone. Yamaguchi esterification was used for (+)-crassalactone B, while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone.
Cytotoxic styryl-lactones from the leaves and twigs of Polyalthia crassa
Tuchinda, Patoomratana,Munyoo, Bamroong,Pohmakotr, Manat,Thinapong, Pongchan,Sophasan, Samaisukh,Santisuk, Thawatchai,Reutrakul, Vichai
, p. 1728 - 1733 (2008/12/21)
Four new styryl-lactones, crassalactones A-D (1-4), were isolated from a cytotoxic ethyl acetate-soluble extract of the leaves and twigs of Polyalthia crassa, together with seven known compounds, (+)-3-acetylaltholactone, (+)-altholactone, aristolactam All, cinnamic acid, (+)-goniofufurone, (+)-goniopypyrone, and (+)-howiinol A. Their structures were determined on the basis of spectroscopic methods. The absolute configuration of 1-3 was established by chemical conversions. Single-crystal X-ray analysis and the Mosher ester method were used to confirm the absolute stereochemistry of 4. Cytotoxic evaluation against several mammalian cancer cell lines was performed on all new isolates, aristolactam AII, and the modified (+)-tricinnamate derivative 11 obtained from 1.
