4.8 Article

Total Synthesis of (-)-Agelastatin A: The Application of a Sequential Sigmatropic Rearrangement

Journal

ORGANIC LETTERS
Volume 11, Issue 12, Pages 2687-2690

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900799e

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan [1320350021]

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An enantioselective total synthesis of (-)-agelastatin A from (-)-2,3-O-isopropylidene-D-threitol is described. The sequential Overman/ Mislow-Evans rearrangement of the allylic bistrichloroimidate is the key step, which efficiently installed a diaminohydroxy group.

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