Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid

Bjorn ter Horst; Jeroen van Wermeskerken; Ben L. Feringa; Adriaan J. Minnaard

doi:10.1002/ejoc.200901120

Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid

Bjorn ter Horst
, Jeroen van Wermeskerken
, Ben L. Feringa^*
, Adriaan J. Minnaard

^*Corresponding author for this work

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

7 Citations (Scopus)

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Abstract

The first asymmetric synthesis of mycolipenic acid and mycolipanolic acid by using an improved iterative procedure involving catalytic asymmetric conjugate addition of MeMgBr as the key step is described. Mycolipenic and mycolipanolic acid are obtained in 11 steps with perfect stereocontrol, and both acids are identical to their counterparts from natural sources.

Original language	English
Pages (from-to)	38-41
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2010
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.200901120
Publication status	Published - Jan-2010

Keywords

Mycolipenic acid
Mycolipanolic acid
Asymmetric synthesis
Mycobacterium tuberculosis
ENANTIOSELECTIVE ALDOL CONDENSATIONS
MYCOBACTERIUM-TUBERCULOSIS
CONJUGATE ADDITION
GRIGNARD-REAGENTS
TREHALOSE
BIOSYNTHESIS
STRAINS

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@article{c7ce8f2d7a32499b84dbf7939c3d48c1,

title = "Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid",

abstract = "The first asymmetric synthesis of mycolipenic acid and mycolipanolic acid by using an improved iterative procedure involving catalytic asymmetric conjugate addition of MeMgBr as the key step is described. Mycolipenic and mycolipanolic acid are obtained in 11 steps with perfect stereocontrol, and both acids are identical to their counterparts from natural sources.",

keywords = "Mycolipenic acid, Mycolipanolic acid, Asymmetric synthesis, Mycobacterium tuberculosis, ENANTIOSELECTIVE ALDOL CONDENSATIONS, MYCOBACTERIUM-TUBERCULOSIS, CONJUGATE ADDITION, GRIGNARD-REAGENTS, TREHALOSE, BIOSYNTHESIS, STRAINS",

author = "\{ter Horst\}, Bjorn and \{van Wermeskerken\}, Jeroen and Feringa, \{Ben L.\} and Minnaard, \{Adriaan J.\}",

year = "2010",

month = jan,

doi = "10.1002/ejoc.200901120",

language = "English",

volume = "2010",

pages = "38--41",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "1",

}

TY - JOUR

T1 - Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid

AU - ter Horst, Bjorn

AU - van Wermeskerken, Jeroen

AU - Feringa, Ben L.

AU - Minnaard, Adriaan J.

PY - 2010/1

Y1 - 2010/1

N2 - The first asymmetric synthesis of mycolipenic acid and mycolipanolic acid by using an improved iterative procedure involving catalytic asymmetric conjugate addition of MeMgBr as the key step is described. Mycolipenic and mycolipanolic acid are obtained in 11 steps with perfect stereocontrol, and both acids are identical to their counterparts from natural sources.

AB - The first asymmetric synthesis of mycolipenic acid and mycolipanolic acid by using an improved iterative procedure involving catalytic asymmetric conjugate addition of MeMgBr as the key step is described. Mycolipenic and mycolipanolic acid are obtained in 11 steps with perfect stereocontrol, and both acids are identical to their counterparts from natural sources.

KW - Mycolipenic acid

KW - Mycolipanolic acid

KW - Asymmetric synthesis

KW - Mycobacterium tuberculosis

KW - ENANTIOSELECTIVE ALDOL CONDENSATIONS

KW - MYCOBACTERIUM-TUBERCULOSIS

KW - CONJUGATE ADDITION

KW - GRIGNARD-REAGENTS

KW - TREHALOSE

KW - BIOSYNTHESIS

KW - STRAINS

U2 - 10.1002/ejoc.200901120

DO - 10.1002/ejoc.200901120

M3 - Article

SN - 1434-193X

VL - 2010

SP - 38

EP - 41

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 1

ER -

Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid

Abstract

Keywords

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