Total Synthesis of (R, R, R)-gamma-Tocopherol through Cu-Catalyzed Asymmetric 1,2-Addition

Zhongtao Wu; Syuzanna R. Harutyunyan; Adriaan J. Minnaard

doi:10.1002/chem.201404458

Total Synthesis of (R, R, R)-gamma-Tocopherol through Cu-Catalyzed Asymmetric 1,2-Addition

Zhongtao Wu
, Syuzanna R. Harutyunyan
, Adriaan J. Minnaard^*

^*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

Based on the asymmetric copper-catalyzed 1,2-addition of Grignard reagents to ketones, (R,R,R)--tocopherol has been synthesized in 36% yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73% ee by the 1,2-addition of a phytol-derived Grignard reagent to an -bromo enone prepared from 2,3-dimethylquinone.

Original language	English
Pages (from-to)	14250-14255
Number of pages	6
Journal	Chemistry
Volume	20
Issue number	44
DOIs	https://doi.org/10.1002/chem.201404458
Publication status	Published - 27-Oct-2014

Keywords

(R
R
R)--tocopherol
1
2-addition
asymmetric catalysis
natural product synthesis
vitamin E
ALPHA-TOCOPHEROL
VITAMIN-E
GAMMA-TOCOPHEROL
ALLYLIC ALKYLATION
GRIGNARD-REAGENTS
NITROGEN-DIOXIDE
HYDROGENATION
OLEFINS
ROUTE
DERIVATIVES

Access to Document

10.1002/chem.201404458

Total Synthesis of (R, R, R)-gamma-Tocopherol through Cu-Catalyzed Asymmetric.pdfFinal publisher's version, 347 KBLicence: Taverne

Handle.net

Persistent link

Cite this

@article{1d7a7605a3c342819a04713134fb5c9f,

title = "Total Synthesis of (R, R, R)-gamma-Tocopherol through Cu-Catalyzed Asymmetric 1,2-Addition",

abstract = "Based on the asymmetric copper-catalyzed 1,2-addition of Grignard reagents to ketones, (R,R,R)--tocopherol has been synthesized in 36\% yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73\% ee by the 1,2-addition of a phytol-derived Grignard reagent to an -bromo enone prepared from 2,3-dimethylquinone.",

keywords = "(R, R, R)--tocopherol, 1, 2-addition, asymmetric catalysis, natural product synthesis, vitamin E, ALPHA-TOCOPHEROL, VITAMIN-E, GAMMA-TOCOPHEROL, ALLYLIC ALKYLATION, GRIGNARD-REAGENTS, NITROGEN-DIOXIDE, HYDROGENATION, OLEFINS, ROUTE, DERIVATIVES",

author = "Zhongtao Wu and Harutyunyan, \{Syuzanna R.\} and Minnaard, \{Adriaan J.\}",

year = "2014",

month = oct,

day = "27",

doi = "10.1002/chem.201404458",

language = "English",

volume = "20",

pages = "14250--14255",

journal = "Chemistry",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag GmbH \& Co. KGaA",

number = "44",

}

TY - JOUR

T1 - Total Synthesis of (R, R, R)-gamma-Tocopherol through Cu-Catalyzed Asymmetric 1,2-Addition

AU - Wu, Zhongtao

AU - Harutyunyan, Syuzanna R.

AU - Minnaard, Adriaan J.

PY - 2014/10/27

Y1 - 2014/10/27

N2 - Based on the asymmetric copper-catalyzed 1,2-addition of Grignard reagents to ketones, (R,R,R)--tocopherol has been synthesized in 36% yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73% ee by the 1,2-addition of a phytol-derived Grignard reagent to an -bromo enone prepared from 2,3-dimethylquinone.

AB - Based on the asymmetric copper-catalyzed 1,2-addition of Grignard reagents to ketones, (R,R,R)--tocopherol has been synthesized in 36% yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73% ee by the 1,2-addition of a phytol-derived Grignard reagent to an -bromo enone prepared from 2,3-dimethylquinone.

KW - (R

KW - R

KW - R)--tocopherol

KW - 1

KW - 2-addition

KW - asymmetric catalysis

KW - natural product synthesis

KW - vitamin E

KW - ALPHA-TOCOPHEROL

KW - VITAMIN-E

KW - GAMMA-TOCOPHEROL

KW - ALLYLIC ALKYLATION

KW - GRIGNARD-REAGENTS

KW - NITROGEN-DIOXIDE

KW - HYDROGENATION

KW - OLEFINS

KW - ROUTE

KW - DERIVATIVES

U2 - 10.1002/chem.201404458

DO - 10.1002/chem.201404458

M3 - Article

SN - 0947-6539

VL - 20

SP - 14250

EP - 14255

JO - Chemistry

JF - Chemistry

IS - 44

ER -

Total Synthesis of (R, R, R)-gamma-Tocopherol through Cu-Catalyzed Asymmetric 1,2-Addition

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Cite this