The Dolastatins. 22. Synthesis of Boc-dolaproinyl dolaphenine and Four Related Chiral Isomers

George Pettit; József Barkóczy; Jayaram K. Srirangam; Sheo Bux Singh; Delbert L. Herald; Michael D. Williams; Darko Kantoci; Fiona Hogan; Thomas L. Groy

doi:10.1021/jo00090a009

The Dolastatins. 22. Synthesis of Boc-dolaproinyl dolaphenine and Four Related Chiral Isomers

George Pettit, József Barkóczy, Jayaram K. Srirangam, Sheo Bux Singh, Delbert L. Herald, Michael D. Williams, Darko Kantoci, Fiona Hogan, Thomas L. Groy

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

10 Scopus citations

Abstract

Synthesis of the dolastatin 10(1) dipeptide segment N-(tert-butoxycarbonyl)-dolaproinyl-dolaphenine (2, Boc-Dap-Doe) and four chiral isomers (3–5, 13) has been summarized. Formation of the amide bond was readily accomplished employing diethyl cyanophosphonate. The stereochemical assignments for Boc-Dap-Doe (2) and Boc-Dap-(6R)-Doe (3) were confirmed by X-ray crystal structure analyses.

Original language	English (US)
Pages (from-to)	2935-2938
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	59
Issue number	11
DOIs	https://doi.org/10.1021/jo00090a009
State	Published - Jun 1 1994

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00090a009

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title = "The Dolastatins. 22. Synthesis of Boc-dolaproinyl dolaphenine and Four Related Chiral Isomers",

abstract = "Synthesis of the dolastatin 10(1) dipeptide segment N-(tert-butoxycarbonyl)-dolaproinyl-dolaphenine (2, Boc-Dap-Doe) and four chiral isomers (3–5, 13) has been summarized. Formation of the amide bond was readily accomplished employing diethyl cyanophosphonate. The stereochemical assignments for Boc-Dap-Doe (2) and Boc-Dap-(6R)-Doe (3) were confirmed by X-ray crystal structure analyses.",

author = "George Pettit and J{\'o}zsef Bark{\'o}czy and Srirangam, {Jayaram K.} and Singh, {Sheo Bux} and Herald, {Delbert L.} and Williams, {Michael D.} and Darko Kantoci and Fiona Hogan and Groy, {Thomas L.}",

year = "1994",

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doi = "10.1021/jo00090a009",

language = "English (US)",

volume = "59",

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T1 - The Dolastatins. 22. Synthesis of Boc-dolaproinyl dolaphenine and Four Related Chiral Isomers

AU - Pettit, George

AU - Barkóczy, József

AU - Srirangam, Jayaram K.

AU - Singh, Sheo Bux

AU - Herald, Delbert L.

AU - Williams, Michael D.

AU - Kantoci, Darko

AU - Hogan, Fiona

AU - Groy, Thomas L.

PY - 1994/6/1

Y1 - 1994/6/1

N2 - Synthesis of the dolastatin 10(1) dipeptide segment N-(tert-butoxycarbonyl)-dolaproinyl-dolaphenine (2, Boc-Dap-Doe) and four chiral isomers (3–5, 13) has been summarized. Formation of the amide bond was readily accomplished employing diethyl cyanophosphonate. The stereochemical assignments for Boc-Dap-Doe (2) and Boc-Dap-(6R)-Doe (3) were confirmed by X-ray crystal structure analyses.

AB - Synthesis of the dolastatin 10(1) dipeptide segment N-(tert-butoxycarbonyl)-dolaproinyl-dolaphenine (2, Boc-Dap-Doe) and four chiral isomers (3–5, 13) has been summarized. Formation of the amide bond was readily accomplished employing diethyl cyanophosphonate. The stereochemical assignments for Boc-Dap-Doe (2) and Boc-Dap-(6R)-Doe (3) were confirmed by X-ray crystal structure analyses.

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The Dolastatins. 22. Synthesis of Boc-dolaproinyl dolaphenine and Four Related Chiral Isomers

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CCDC 125579: Experimental Crystal Structure Determination

CCDC 125556: Experimental Crystal Structure Determination

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The Dolastatins. 22. Synthesis of Boc-dolaproinyl dolaphenine and Four Related Chiral Isomers

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 125579: Experimental Crystal Structure Determination

CCDC 125556: Experimental Crystal Structure Determination

Cite this