Suzuki-Miyaura and Stille reactions as key steps in the synthesis of diversely functionalized Amaryllidaceae alkaloid analogs bearing a 5,6,7,8-tetrahydrobenzo[c,e]azocine skeleton.

Abstract:

:Microwave-assisted Suzuki-Miyaura and Stille cross-coupling reactions for the synthesis of highly electron-rich and diversely functionalized biaryl intermediates are presented. Microwave-irradiation has been demonstrated to be a very powerful tool for performing difficult transition metal-catalyzed cross-coupling reactions with unfavorably substituted coupling partners. The key biaryl intermediates were used for the microwave-enhanced construction of the 5,6,7,8-tetrahydrobenzo[c,e]azocine skeleton of the Apogalanthamine analogs. The success of the strategy is demonstrated by synthesizing a number of hitherto unknown, diversely functionalized, natural product analogs.

authors

Appukkuttan P,Dehaen W,Van der Eycken E

doi

10.2174/138620707783018513

subject

Has Abstract

pub_date

2007-11-01 00:00:00

pages

790-801

issue

9

eissn

1386-2073

issn

1875-5402

journal_volume

10

pub_type

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