(+)- and (-)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity
(+)- and (-)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity
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DOI：
10.1021/jo9000405
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发表时间：
2009-03-20
影响因子：
3.6
通讯作者：
Silva, Luiz F., Jr.
中科院分区：
文献类型：
--
作者：
Bianco, Graziela G.;Ferraz, Helena M. C.;Silva, Luiz F., Jr.
以2-甲基苯甲醚为起始原料，经11步反应首次合成了天然产物（+）-木桐酚，总收率21%。其对映异构体的合成也以类似的总产率进行。倍半萜（+）-mutisianthol的绝对构型为（1 S，3R）。该路线的关键步骤是使用手性铱催化剂对非官能化烯烃进行不对称氢化，以及使用铊（III）或碘（III）对1，2-二氢萘进行环收缩。靶分子对人肿瘤细胞系SF-295、HCT-8和MDA-MB-435显示出中等活性。
The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.