Efficient Enantio- and Diastereodivergent Synthesis of Poison-Frog Alkaloids 251O and trans-223B

An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R = n-C7H15, R′ = n-Pr) and 14 by...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-09, Vol.74 (17), p.6784-6791
Main Authors: Toyooka, Naoki, Zhou, Dejun, Nemoto, Hideo, Tezuka, Yasuhiro, Kadota, Shigetoshi, Andriamaharavo, Nirina R, Garraffo, H. Martin, Spande, Thomas F, Daly, John W
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkenes - chemistry
Animals
Chemistry, Organic - methods
Chromatography, Gas - methods
Drug Design
Kinetics
Models, Chemical
Poisons - chemistry
Pyrroles - chemistry
Pyrrolizidine Alkaloids - chemistry
Ranidae
Spectroscopy, Fourier Transform Infrared - methods
Stereoisomerism
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Summary:An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R = n-C7H15, R′ = n-Pr) and 14 by the present enantioselective synthesis.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901100m