Hyperjovinol B (1)與empetriferdinan A (2)這兩個天然物皆被發現於金絲桃科(Clusiaceae)植物中，金絲桃科植物為一在東西方皆常見的傳統草藥。Hyperjovinol B (1)與empetriferdinan A (2)其結構皆為一tricyclic acylphloroglucinol的三環結構，其中擁有一個單萜部分，並接有一個isobutyryl group，其立體化學在4a位置上的甲基與9a位置上的氫為trans組態。
Hyperjuvinol B (1)與empetriferdinan A (2)為兩個分別具有抗氧化及抗癌生物活性的天然物，目前皆尚未有全合成之報導，為了進一步探討其結構與活性間之關係，在本研究中預計建立一有效的合成方法來合成具有絕對立體構型的化合物 1、2及類似物。
Hyperjuvinol B (1)與empetriferdinan A (2)的全合成以1,3,5-trimethoxybenzene與cyclogeranic acid為起始物，目前已經由九個合成步驟製備出重要的中間產物Ger220，之後再經由五個步驟將合成出天然物1和2及其它立體異構物，這些合成的化合物將被探討其生物活性。
Naturally occurring hyperjovinol B (1) and empetriferdinan A (2) were isolated and characterized from Hypericum (Clusiaceae) plants. Hypericum plants are used as traditional herbs in Eastern and Western. The structure of hyperjovinol B (1) and empetriferdinan A (2) is a tricyclic acylphloroglucinol possessing a monoterpenoid moiety and a isobutyryl group. The stereochemistry of 1 and 2 showed that a methyl group in 4a position and a hydrogen atom in 9a position are in trans configuration.
Hyperjuvinol B (1) and empetriferdinan A (2) showed antioxidant and antitumor activity, respectively. Until now, the total synthesis of 1 and 2 has not been reported yet. To further explore the structure and activity relationship, in this thesis, an efficient synthetic method was carried out to prepare the compounds 1 and 2 with absolute configuration.
Hyperjuvinol B (1) and empetriferdinan A (2) were synthesized starting from 1,3,5-trimethoxybenzene and cyclogeranic acid. So far, the key intermediate (Ger220) was successfully prepared in nine steps. Natural products 1 and 2 as well as their stereoisomers will be synthesized in five steps from Ger220. The biological activity of all the synthesized compounds will be evaluated in the near future.
