The dolastatins. 19. Synthesis of dolaisoleuine

George Pettit, Sheo Bux Singh, Jayaram K. Srirangam, Fiona Hogan-Pierson, Michael D. Williams

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The synthesis of dolaisoleuine as its tert-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinal and tert-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.

Original languageEnglish (US)
Pages (from-to)1796-1800
Number of pages5
JournalJournal of Organic Chemistry
Volume59
Issue number7
StatePublished - 1994

Fingerprint

dolastatin 10
Amino Acids
Methylation
Condensation
Esters
tert-butyl acetate
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Pettit, G., Singh, S. B., Srirangam, J. K., Hogan-Pierson, F., & Williams, M. D. (1994). The dolastatins. 19. Synthesis of dolaisoleuine. Journal of Organic Chemistry, 59(7), 1796-1800.

The dolastatins. 19. Synthesis of dolaisoleuine. / Pettit, George; Singh, Sheo Bux; Srirangam, Jayaram K.; Hogan-Pierson, Fiona; Williams, Michael D.

In: Journal of Organic Chemistry, Vol. 59, No. 7, 1994, p. 1796-1800.

Research output: Contribution to journalArticle

Pettit, G, Singh, SB, Srirangam, JK, Hogan-Pierson, F & Williams, MD 1994, 'The dolastatins. 19. Synthesis of dolaisoleuine', Journal of Organic Chemistry, vol. 59, no. 7, pp. 1796-1800.
Pettit G, Singh SB, Srirangam JK, Hogan-Pierson F, Williams MD. The dolastatins. 19. Synthesis of dolaisoleuine. Journal of Organic Chemistry. 1994;59(7):1796-1800.
Pettit, George ; Singh, Sheo Bux ; Srirangam, Jayaram K. ; Hogan-Pierson, Fiona ; Williams, Michael D. / The dolastatins. 19. Synthesis of dolaisoleuine. In: Journal of Organic Chemistry. 1994 ; Vol. 59, No. 7. pp. 1796-1800.
@article{f3c72cecae9c4951a08d00dd03d698cf,
title = "The dolastatins. 19. Synthesis of dolaisoleuine",
abstract = "The synthesis of dolaisoleuine as its tert-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinal and tert-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.",
author = "George Pettit and Singh, {Sheo Bux} and Srirangam, {Jayaram K.} and Fiona Hogan-Pierson and Williams, {Michael D.}",
year = "1994",
language = "English (US)",
volume = "59",
pages = "1796--1800",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

T1 - The dolastatins. 19. Synthesis of dolaisoleuine

AU - Pettit, George

AU - Singh, Sheo Bux

AU - Srirangam, Jayaram K.

AU - Hogan-Pierson, Fiona

AU - Williams, Michael D.

PY - 1994

Y1 - 1994

N2 - The synthesis of dolaisoleuine as its tert-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinal and tert-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.

AB - The synthesis of dolaisoleuine as its tert-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinal and tert-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.

UR - http://www.scopus.com/inward/record.url?scp=0028226107&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028226107&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0028226107

VL - 59

SP - 1796

EP - 1800

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 7

ER -