A new efficient synthetic process for the construction of the pentacyclic core of marine alkaloid ecteinascidins

The pentacyclic core of ecteinascidins was constructed from two fundamental building blocks, the 1,2,3,4-tetrahydroisoquinoline derivative and the substituted phenylalanine derivative, via 8 steps using readily available L-Dopa as starting material. The key steps involve coupling of the two aforemen...

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Bibliographic Details
Published in:Tetrahedron letters 2003-09, Vol.44 (37), p.7091-7094
Main Authors: Tang, Ye-Feng, Liu, Zhan-Zhu, Chen, Shi-Zhi
Format: Article
Language:English
Subjects:
ecteinascidins
L-Dopa
pentacyclic core
Pictet–Spengler cyclization
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Summary:The pentacyclic core of ecteinascidins was constructed from two fundamental building blocks, the 1,2,3,4-tetrahydroisoquinoline derivative and the substituted phenylalanine derivative, via 8 steps using readily available L-Dopa as starting material. The key steps involve coupling of the two aforementioned building blocks, regioselective reduction of the 11-carbonyl group of the key intermediate piperazine-1,4-dione derivative, and intramolecular Pictet–Spengler cyclization. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)01785-4