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Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

ABSTRACT: [Structure: see text] A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.

SUBMITTER: Mejia-Oneto JM

PROVIDER: S-EPMC2604816 | biostudies-literature | 2006 Jul

REPOSITORIES: biostudies-literature

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Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

Mejía-Oneto José M JM Padwa Albert A

Organic letters 20060701 15

[Structure: see text] A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction. ...[more]

PMID: 16836384

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