Synthesis of vinca alkaloids and related compounds.: Part 109.: An intramolecular [4+2] cycloaddition mediated biomimetic synthesis of (+/-)-iboxyphylline

被引：0
|
作者：
Toth, Florian [1 ]
Kalaus, Gyoergy [1 ]
Pipa, Gergely [1 ]
Greiner, Istvan [2 ]
Szollosy, Aron [3 ]
Rill, Attila [2 ]
Gomory, Agnes [4 ]
Hazai, Laszlo [1 ]
Szantay, Csaba [1 ,4 ]
机构：
[1] Budapest Univ Technol & Econ, Hungarian Acad Sci, Dept Organ Chem & Technol, Res Grp Alkaloid Chem, H-1521 Budapest, Hungary
[2] Gedeon Richter Chem Works Ltd, Chem Works, H-1103 Budapest, Hungary
[3] Budapest Univ Technol & Econ, Dept Inorgan & Analyt Chem, H-1521 Budapest, Hungary
[4] Hungarian Acad Sci, Chem Res Ctr, Inst Chem, H-1025 Budapest, Hungary
来源：
HETEROCYCLES | 2008年 / 75卷 / 01期
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D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The pentacyclic alkaloid 1 could be synthesized by an intramolecular [4+2] cycloaddition reaction of intermediate 11, which had been obtained from tryptamine derivative 4 and aldehyde 5. After full epimerization of 13 the cyclization reaction furnished a mixture of 14a and 14b. Separation of the stereoisomers 14a and 14b and subsequent reduction with LiAlH4 resulted in (+/-)-iboxyphylline (14a -> 1) and its epimer, (+/-)-20-epiiboxyphylline (14b -> 15).
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页码：65 / 76
页数：12
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