Synthesis of Natural Lignans and Their Derivatives
Date Issued
2004
Date
2004
Author(s)
Wein, Yung-Shung
DOI
zh-TW
Abstract
A convenient and facile approach to synthesize salvinal was developed. Meanwhile 32 salvinal derivatives with the benzofuran skeleton were also synthesized. They differ in the substitutes at the C-3, C-5 position of the benzofuran skeleton and the phenyl group. These differences influence their biological activities, and therefore the structure-activity-relationship can be established.
We applied two Stobbe reaction steps to synthesize taiwanin A derivatives, and to investigate their inhibitory activity on the growth of HONE-1 cell. The mechanism of photooxygenation of taiwanin A to taiwanin C and taiwanin E was also discussed. The yield was improved under low temperature and bubbling oxygen gas when lighting, fewer side products and higher yield was observed. We also transfered taiwanin A to dihydrotaiwanin C in the acidic condition to get the products of 1-aryl-1,4-dihydronaphthalene lignanlactone.
Confirming the structures of new natural products by partial synthesis or synthesis also performed in the third part. We designed the shortest pathway to synthesize obtusal A, obtusal B and 5-(2-hydroxyphenoxymethyl)furfural.
Subjects
抗有絲分裂
阿伯勒
木酚素
丹參
Salvia mitorrhiza
lignan
Taiwannia cryptomerioides
antimitotic
Chamaecyparis obtusa var. formosana
Cassia fistula
Type
thesis