Synthetic process toward total synthesis of eleutherobin and its analogues and uses thereof

US6172205A · kind A · utility

Assignee

• The Trustees of Columbia in the City of New York · US

Inventors

• Samuel J. Danishefsky · New Haven, US
• Xiao-Tao Chen · New York, US
• Clare E. Gutteridge · Annapolis, US
• Samit Kumar Bhattacharya · Groton, US
• Bishan Zhou · Edison, US

Key dates

• Filing date: Dec 11, 1998
• Grant date: Jan 9, 2001
• Expiry date: Dec 11, 2018

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H17/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention provides a process for the preparation of a Eleutherobin derivative of the formula: ##STR1## wherein R.sub.1 is a hydrogen, ester, nitrile or C.sub.2 H.sub.4 --R wherein R.sub.4 is a carbohydrate, an alcohol an amine, an amide, an alkyne, or, R.sub.2 is a linear or branched alkyl moiety, R.sub.3 is an ester, an amide, a carbamate, an acetal compound,an ether or a urethane, R.sub.4 is a hydrogen or CH.sub.2,position C.sub.2 and C.sub.3 is cis or trans,position C.sub.8 is .alpha. or .beta. and a compound is produced having the structures: ##STR2## Additionally, this experiment provides a method for inhibiting growth of cancerous cells comprising contracting an amount of Eleutherobin derivative effective to inhibit the growth of said cells. Further provided is a method for treating cancer in a subject which comprises administering to the subject a therapeutically effective amount of the Eleutherobin derivative.