Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation

Christopher J. Bartlett; David P. Day; Yohan Chan; Steven M. Allin; Michael J. McKenzie; Alexandra M. Z. Slawin; Philip C. Bulman Page

doi:10.1021/jo2021407

Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation

Christopher J. Bartlett, David P. Day, Yohan Chan, Steven M. Allin, Michael J. McKenzie, Alexandra M. Z. Slawin, Philip C. Bulman Page

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

Abstract

We report the first enantioselective total synthesis of (+)-scuteflorin A in 14% overall yield, employing a chiral iminium salt to effect an organocatalytic asymmetric epoxidation of xanthyletin in >99% ee as the key step.

Original language	English
Pages (from-to)	772-774
Number of pages	3
Journal	The Journal of Organic Chemistry
Volume	77
Issue number	1
DOIs	https://doi.org/10.1021/jo2021407
Publication status	Published - 6 Jan 2012

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

IMINIUM SALTS
SCUTELLARIA-LATERIFLORA
ANGELICA-DECURSIVA
CANCER CELLS
STEREOSTRUCTURES
(+)-DECURSINOL
CATALYSTS
COUMARIN

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10.1021/jo2021407

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title = "Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation",

abstract = "We report the first enantioselective total synthesis of (+)-scuteflorin A in 14\% overall yield, employing a chiral iminium salt to effect an organocatalytic asymmetric epoxidation of xanthyletin in >99\% ee as the key step.",

keywords = "IMINIUM SALTS, SCUTELLARIA-LATERIFLORA, ANGELICA-DECURSIVA, CANCER CELLS, STEREOSTRUCTURES, (+)-DECURSINOL, CATALYSTS, COUMARIN",

author = "Bartlett, \{Christopher J.\} and Day, \{David P.\} and Yohan Chan and Allin, \{Steven M.\} and McKenzie, \{Michael J.\} and Slawin, \{Alexandra M. Z.\} and Page, \{Philip C. Bulman\}",

year = "2012",

month = jan,

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doi = "10.1021/jo2021407",

language = "English",

volume = "77",

pages = "772--774",

journal = "The Journal of Organic Chemistry",

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publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation

AU - Bartlett, Christopher J.

AU - Day, David P.

AU - Chan, Yohan

AU - Allin, Steven M.

AU - McKenzie, Michael J.

AU - Slawin, Alexandra M. Z.

AU - Page, Philip C. Bulman

PY - 2012/1/6

Y1 - 2012/1/6

N2 - We report the first enantioselective total synthesis of (+)-scuteflorin A in 14% overall yield, employing a chiral iminium salt to effect an organocatalytic asymmetric epoxidation of xanthyletin in >99% ee as the key step.

AB - We report the first enantioselective total synthesis of (+)-scuteflorin A in 14% overall yield, employing a chiral iminium salt to effect an organocatalytic asymmetric epoxidation of xanthyletin in >99% ee as the key step.

KW - IMINIUM SALTS

KW - SCUTELLARIA-LATERIFLORA

KW - ANGELICA-DECURSIVA

KW - CANCER CELLS

KW - STEREOSTRUCTURES

KW - (+)-DECURSINOL

KW - CATALYSTS

KW - COUMARIN

UR - https://www.scopus.com/pages/publications/84855558439

U2 - 10.1021/jo2021407

DO - 10.1021/jo2021407

M3 - Article

SN - 0022-3263

VL - 77

SP - 772

EP - 774

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 1

ER -

Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation

Abstract

UN SDGs

Keywords

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