Highly enantioselective total synthesis of (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone

Philip C. Bulman Page; Louise F. Appleby; David Day; Yohan Chan; Benjamin R. Buckley; Steven M. Allin; Michael J. McKenzie

doi:10.1021/ol900444h

Highly enantioselective total synthesis of (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone

Philip C. Bulman Page, Louise F. Appleby, David Day, Yohan Chan, Benjamin R. Buckley, Steven M. Allin, Michael J. McKenzie

Chemistry of Materials and Catalysis

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

48 Citations (Scopus)

Abstract

Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.

Original language	English
Pages (from-to)	1991-1993
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	9
DOIs	https://doi.org/10.1021/ol900444h
Publication status	Published - 8 Apr 2009

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10.1021/ol900444h

Cite this

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title = "Highly enantioselective total synthesis of (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone",

abstract = "Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.",

author = "{Bulman Page}, {Philip C.} and Appleby, {Louise F.} and David Day and Yohan Chan and Buckley, {Benjamin R.} and Allin, {Steven M.} and McKenzie, {Michael J.}",

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language = "English",

volume = "11",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

number = "9",

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T1 - Highly enantioselective total synthesis of (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone

AU - Bulman Page, Philip C.

AU - Appleby, Louise F.

AU - Day, David

AU - Chan, Yohan

AU - Buckley, Benjamin R.

AU - Allin, Steven M.

AU - McKenzie, Michael J.

PY - 2009/4/8

Y1 - 2009/4/8

N2 - Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.

AB - Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.

U2 - 10.1021/ol900444h

DO - 10.1021/ol900444h

M3 - Article

SN - 1523-7052

VL - 11

SP - 1991

EP - 1993

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -