Chemoenzymatic Total Synthesis of (+)‐Galanthamine and (+)‐Narwedine from Phenethyl Acetate,Chemistry - A European Journal

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Chemoenzymatic Total Synthesis of (+)‐Galanthamine and (+)‐Narwedine from Phenethyl Acetate
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-08-26 , DOI: 10.1002/chem.201603735
Mary A. A. Endoma-Arias ₁ , Tomas Hudlicky ₁

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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.

中文翻译：

乙酸苯乙酯化学合成酶法合成（+）-加兰他敏和（+）-Narwedine

描述了从乙酸苯乙酯开始的非天然（+）-加兰他敏的立体选择性全合成。手性是通过将重组菌株JM109（pDTG601A）将乙酸苯乙酯进行微生物二羟基化作用而引入相应的顺式-环己二烯二醇，其构型提供了（+）-加兰他敏C环的绝对立体化学。分子内Heck环化用于形成季碳和二苯并呋喃官能团。（+）-加兰他敏的合成分十步完成，总产率为5.5％。提供了所有新化合物的实验数据和光谱数据。

更新日期：2016-08-26

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