Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction

S.F. Mayer; A. Steinreiber; R.V.A. Orru; K.A. Faber

doi:10.1021/jo020073w

Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction

S.F. Mayer
, A. Steinreiber
, R.V.A. Orru
, K.A. Faber

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

Abstract

Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

Original language	English
Pages (from-to)	9115-9121
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	67
Issue number	26
Early online date	11 Jun 2002
DOIs	https://doi.org/10.1021/jo020073w
Publication status	Published - 1 Dec 2002

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@article{b2f1dfa82a5a4a99b56ea19982ac46c9,

title = "Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction",

abstract = "Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.",

author = "S.F. Mayer and A. Steinreiber and R.V.A. Orru and K.A. Faber",

year = "2002",

month = dec,

day = "1",

doi = "10.1021/jo020073w",

language = "English",

volume = "67",

pages = "9115--9121",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "26",

}

Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction. / Mayer, S.F.; Steinreiber, A.; Orru, R.V.A. et al.
In: Journal of Organic Chemistry, Vol. 67, No. 26, 01.12.2002, p. 9115-9121.

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

TY - JOUR

T1 - Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction

AU - Mayer, S.F.

AU - Steinreiber, A.

AU - Orru, R.V.A.

AU - Faber, K.A.

PY - 2002/12/1

Y1 - 2002/12/1

N2 - Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

AB - Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

U2 - 10.1021/jo020073w

DO - 10.1021/jo020073w

M3 - Article

SN - 0022-3263

VL - 67

SP - 9115

EP - 9121

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -