Total Synthesis of Lamellarins D, H, and R and Ningalin B

A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving an AgOAc-mediated oxidative co...

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Bibliographic Details
Published in:Organic letters 2011-01, Vol.13 (2), p.312-315
Main Authors: Li, Qingjiang, Jiang, Jingqian, Fan, Aili, Cui, Yuxin, Jia, Yanxing
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkaloids - chemical synthesis
Alkaloids - chemistry
Amines - chemistry
Catalysis
Coumarins - chemical synthesis
Coumarins - chemistry
Cyclization
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Marine Biology
Molecular Structure
Oxidation-Reduction
Pyrroles - chemical synthesis
Pyrroles - chemistry
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Summary:A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving an AgOAc-mediated oxidative coupling reaction to construct the pyrrole core, a Pb(OAc)4-induced oxidative cyclization to form the lactone, and Kita’s oxidation reaction to form the pyrrole−arene C−C bond.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1027877