Tetrahedron Asymmetry

, volume 7 , issue 11 , pages 3255-3262

Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid

Barbara Jakob ¹

Gundula Voss ¹

Hans Gerlach ¹

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Laboratory of Organic Chemistry, University of Bayreuth, D-95440 Bayreuth, Germany |

Publication type: Journal Article

Publication date: 1996-11-01

Elsevier

Tetrahedron Asymmetry

SJR: —

CiteScore: —

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ISSN: 09574166, 1362511X

DOI: 10.1016/0957-4166(96)00426-0

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Catalysis

Organic Chemistry

Inorganic Chemistry

Physical and Theoretical Chemistry

Abstract

Diol (R)-(+)- 3 is prepared either from the hydroxyketone 2 by reduction with fermenting baker's yeast or by hydrolysis of the dioxolane (R)-(+)- 1 which is available from dimethyl d -malate as starting material. (R)-(+)- 3 could be converted stereoselectively into (R)-(+)- 4 . Reaction of (+)- 4 with dodecylmagnesium bromide yielded the alcohol (S)-(−)- 5 with >99% ee. Its acetylation gave (S)-(+)- 6 and hydrogenolysis gave the primary alcohol (S)-(+)- 7 which could be oxidized selectively to (S)-(+)- 8 with NaIO 4 RuCl 3 . Alkaline hydroysis of (+)- 8 yielded 3-hydroxyhexadecanoic acid (S)-(+)- 9 which could be esterified to give the methyl ester (S)-(+)- 10 with >99% ee. Starting with the dioxolane (S)-(−)- 1 , derived from dimethyl l -malate, the 3-hydroxyhexadecanoic acid (R)-(−)- 9 and its methyl ester (R)-(−)- 10 could be synthesized via the intermediates (S)-(−)- 3 , (S)-(−)- 4 , (R)-(+)- 5 , (R)-(−)- 6 , (R)-(−)- 7 and (R)-(−)- 8 . Graphic

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Jakob B., Voss G., Gerlach H. Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid // Tetrahedron Asymmetry. 1996. Vol. 7. No. 11. pp. 3255-3262.

GOST all authors (up to 50) Copy

Jakob B., Voss G., Gerlach H. Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid // Tetrahedron Asymmetry. 1996. Vol. 7. No. 11. pp. 3255-3262.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/0957-4166(96)00426-0

UR - https://doi.org/10.1016/0957-4166(96)00426-0

TI - Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid

T2 - Tetrahedron Asymmetry

AU - Jakob, Barbara

AU - Voss, Gundula

AU - Gerlach, Hans

PY - 1996

DA - 1996/11/01

PB - Elsevier

SP - 3255-3262

IS - 11

VL - 7

SN - 0957-4166

SN - 1362-511X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{1996_Jakob,

author = {Barbara Jakob and Gundula Voss and Hans Gerlach},

title = {Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid},

journal = {Tetrahedron Asymmetry},

year = {1996},

volume = {7},

publisher = {Elsevier},

month = {nov},

url = {https://doi.org/10.1016/0957-4166(96)00426-0},

number = {11},

pages = {3255--3262},

doi = {10.1016/0957-4166(96)00426-0}

}

MLA

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MLA Copy

Jakob, Barbara, et al. “Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid.” Tetrahedron Asymmetry, vol. 7, no. 11, Nov. 1996, pp. 3255-3262. https://doi.org/10.1016/0957-4166(96)00426-0.

Publisher

Elsevier

Journal

Tetrahedron Asymmetry

SJR

—

CiteScore

—

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—

ISSN

09574166 (Print)

1362511X (Electronic)