Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate
Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate
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DOI：
10.1002/chem.201603735
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发表时间：
2016-10-01
影响因子：
4.3
通讯作者：
Hudlicky, Tomas
中科院分区：
文献类型：
--
作者：
Endoma-Arias, Mary A. A.;Hudlicky, Tomas
报道了以乙酸苯乙酯为起始原料立体选择性全合成非天然（+）-加兰他敏的方法。手性通过微生物双羟基化乙酸苯乙酯与重组菌株JM 109（pDTG 601 A）引入到相应的顺式-环己二烯，其构型提供了（+）-加兰他敏的环C的绝对立体化学。分子内Heck环化用于形成季碳和二苯并呋喃官能团。（+）-加兰他敏的合成共经10步反应完成，总收率为5.5%。实验和光谱数据提供了所有新的化合物。
The stereoselective total synthesis of unnatural (+)-galanthamine starting from phenethyl acetate is described. Chirality was introduced via microbial dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) to the corresponding cis-cyclohexadi-enediol, configuration of which provided the absolute stereochemistry of the ring C of (+)-galanthamine. Intramolecular Heck cyclization was used to form the quaternary carbon and dibenzofuran functionality. The synthesis of (+)-galanthamine was completed in a total of ten steps and an overall yield of 5.5%. Experimental and spectral data are provided for all new compounds.