THE DOLASTATINS .22. SYNTHESIS OF BOC-DOLAPROINYL-DOLAPHENINE AND 4 RELATED CHIRAL ISOMERS

Authors
PETTIT GR BARKOCZY J SRIRANGAM JK SINGH SB HERALD DL WILLIAMS MD KANTOCI D HOGAN F GROY TL
Citation
Gr. Pettit et al., THE DOLASTATINS .22. SYNTHESIS OF BOC-DOLAPROINYL-DOLAPHENINE AND 4 RELATED CHIRAL ISOMERS, Journal of organic chemistry, 59(11), 1994, pp. 2935-2938
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
11
Year of publication
1994
Pages
2935 - 2938
Database
ISI
SICI code
0022-3263(1994)59:11<2935:TD.SOB>2.0.ZU;2-5
Abstract
Synthesis of the dolastatin 10 (1) dipeptide segment N-(tert-butoxycar bonyl)-dolaproinyl-dolaphenine (2, Boc-Dap-Doe) and four chiral isomer s (3-5, 13) has been summarized. Formation of the amide bond was readi ly accomplished employing diethyl cyanophosphonate. The stereochemical assignments for Boc-Dap-Doe (2) and Boc-Dap-(6R)-Doe (3) were confirm ed by X-ray crystal structure analyses.