Synthesis of (S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, a precursor to the unusual amino acid residue of the anticancer agent microsporin B

Wenxin Gu; Richard B. Silverman

doi:10.1016/j.tetlet.2011.07.132

Synthesis of (S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, a precursor to the unusual amino acid residue of the anticancer agent microsporin B

Wenxin Gu, Richard B. Silverman^*

^*Corresponding author for this work

Chemistry

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

7 Scopus citations

Abstract

(S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, the Boc-protected precursor of an unusual amino acid residue for the synthesis of microsporin B, was synthesized. The key steps include a Suzuki coupling followed by asymmetric homogeneous hydrogenation.

Original language	English (US)
Pages (from-to)	5438-5440
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2011.07.132
State	Published - Oct 19 2011

Funding

The authors are grateful to the National Institutes of Health (Grant R41 CA116971 ) for financial support of this research.

Keywords

Amino acid
Asymmetric homogeneous hydrogenation
Cyclic tetrapeptide
HDAC
Microsporin
Olefin metathesis
Suzuki coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of (S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, a precursor to the unusual amino acid residue of the anticancer agent microsporin B",

abstract = "(S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, the Boc-protected precursor of an unusual amino acid residue for the synthesis of microsporin B, was synthesized. The key steps include a Suzuki coupling followed by asymmetric homogeneous hydrogenation.",

keywords = "Amino acid, Asymmetric homogeneous hydrogenation, Cyclic tetrapeptide, HDAC, Microsporin, Olefin metathesis, Suzuki coupling",

author = "Wenxin Gu and Silverman, {Richard B.}",

note = "Funding Information: The authors are grateful to the National Institutes of Health (Grant R41 CA116971 ) for financial support of this research. ",

year = "2011",

month = oct,

day = "19",

doi = "10.1016/j.tetlet.2011.07.132",

language = "English (US)",

volume = "52",

pages = "5438--5440",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "42",

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TY - JOUR

T1 - Synthesis of (S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, a precursor to the unusual amino acid residue of the anticancer agent microsporin B

AU - Gu, Wenxin

AU - Silverman, Richard B.

N1 - Funding Information: The authors are grateful to the National Institutes of Health (Grant R41 CA116971 ) for financial support of this research.

PY - 2011/10/19

Y1 - 2011/10/19

N2 - (S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, the Boc-protected precursor of an unusual amino acid residue for the synthesis of microsporin B, was synthesized. The key steps include a Suzuki coupling followed by asymmetric homogeneous hydrogenation.

AB - (S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, the Boc-protected precursor of an unusual amino acid residue for the synthesis of microsporin B, was synthesized. The key steps include a Suzuki coupling followed by asymmetric homogeneous hydrogenation.

KW - Amino acid

KW - Asymmetric homogeneous hydrogenation

KW - Cyclic tetrapeptide

KW - HDAC

KW - Microsporin

KW - Olefin metathesis

KW - Suzuki coupling

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DO - 10.1016/j.tetlet.2011.07.132

M3 - Article

C2 - 21984850

AN - SCOPUS:80052787688

SN - 0040-4039

VL - 52

SP - 5438

EP - 5440

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Synthesis of (S)-2-Boc-Amino-8-(R)-(tert-butyldimethylsilanyloxy)decanoic acid, a precursor to the unusual amino acid residue of the anticancer agent microsporin B

Abstract

Funding

Keywords

ASJC Scopus subject areas

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