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

关键词：

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).

引用

页码：65 / 76

页数：12

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