Total synthesis and structural revision of the alkaloid IncargranineB

Patrick D. Brown; Anthony C. Willis; Michael S. Sherburn; Andrew L. Lawrence

doi:10.1002/anie.201307875

Total synthesis and structural revision of the alkaloid IncargranineB

Patrick D. Brown, Anthony C. Willis^*, Michael S. Sherburn, Andrew L. Lawrence

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

Abstract

Seeing double: Consideration of the biosynthetic origins of incargranineB, which was originally assigned an unprecedented indolo[1.7]naphthyridine structure, led to the proposal of a dipyrroloquinoline framework as a more biosynthetically feasible structure (see scheme; Piv=pivaloyl). This hypothesis was validated by a short biomimetic synthesis of incargranineB.

Original language	English
Pages (from-to)	13273-13275
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	50
DOIs	https://doi.org/10.1002/anie.201307875
Publication status	Published - 9 Dec 2013

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abstract = "Seeing double: Consideration of the biosynthetic origins of incargranineB, which was originally assigned an unprecedented indolo[1.7]naphthyridine structure, led to the proposal of a dipyrroloquinoline framework as a more biosynthetically feasible structure (see scheme; Piv=pivaloyl). This hypothesis was validated by a short biomimetic synthesis of incargranineB.",

keywords = "alkaloids, biomimetic synthesis, domino reactions, natural products, structural reassignment",

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AU - Willis, Anthony C.

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AU - Lawrence, Andrew L.

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AB - Seeing double: Consideration of the biosynthetic origins of incargranineB, which was originally assigned an unprecedented indolo[1.7]naphthyridine structure, led to the proposal of a dipyrroloquinoline framework as a more biosynthetically feasible structure (see scheme; Piv=pivaloyl). This hypothesis was validated by a short biomimetic synthesis of incargranineB.

KW - alkaloids

KW - biomimetic synthesis

KW - domino reactions

KW - natural products

KW - structural reassignment

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DO - 10.1002/anie.201307875

M3 - Article

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EP - 13275

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Total synthesis and structural revision of the alkaloid IncargranineB

Abstract

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