Enantioselective total synthesis of (-)-diversonol.
Enantioselective total synthesis of (-)-diversonol.
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DOI：
10.1002/chem.201204037
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发表时间：
2013-04
期刊：
影响因子：
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通讯作者：
L. Tietze;Stefan Jackenkroll;C. Raith;Dirk A. Spiegl;Johannes R. Reiner;Maria Claudia Ochoa Campos
中科院分区：
文献类型：
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作者：
L. Tietze;Stefan Jackenkroll;C. Raith;Dirk A. Spiegl;Johannes R. Reiner;Maria Claudia Ochoa Campos
在（-）-diversonol（ent-1）的合成中，采用了对映选择性的domino-Wacker/羰基化/甲氧基化反应和对映选择性的Wacker氧化反应，以较高的收率分别得到96%和93%ee的苯并二氢吡喃。使用Sharpless程序和Wittig-Horner反应在乙烯基部分进行二羟基化，然后进行氢化、苄基氧化和分子内酰化，得到四羟基蒽酮，其中ent-1可以通过几个步骤获得。此外，还描述了非对映异构体diversonol rac-1，9a-表-diversonol（rac-41）的合成。
For the synthesis of (-)-diversonol (ent-1), an enantioselective domino-Wacker/carbonylation/methoxylation reaction and an enantioselective Wacker oxidation were used to give the chroman in high yield and 96% and 93% ee, respectively. Dihydroxylation at the vinyl moiety using the Sharpless procedure and a Wittig-Horner reaction followed by hydrogenation, benzylic oxidation, and an intramolecular acylation provided the tetrahydroxanthenone, from which ent-1 is accessible in a few steps. Furthermore, the synthesis of the diastereomeric diversonol rac-1,9a-epi-diversonol (rac-41) is also described.