WO2006055578A3 - Asymmetric synthesis of (-)-agelastatin a - Google Patents

Asymmetric synthesis of (-)-agelastatin a Download PDF

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Publication number
WO2006055578A3
WO2006055578A3 PCT/US2005/041418 US2005041418W WO2006055578A3 WO 2006055578 A3 WO2006055578 A3 WO 2006055578A3 US 2005041418 W US2005041418 W US 2005041418W WO 2006055578 A3 WO2006055578 A3 WO 2006055578A3
Authority
WO
WIPO (PCT)
Prior art keywords
agelastatin
asymmetric synthesis
diamino
derived
sulfinimine
Prior art date
Application number
PCT/US2005/041418
Other languages
French (fr)
Other versions
WO2006055578A2 (en
Inventor
Franklin A Davis
Jianghe Deng
Original Assignee
Higher Education Temple Univer
Franklin A Davis
Jianghe Deng
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Higher Education Temple Univer, Franklin A Davis, Jianghe Deng filed Critical Higher Education Temple Univer
Publication of WO2006055578A2 publication Critical patent/WO2006055578A2/en
Publication of WO2006055578A3 publication Critical patent/WO2006055578A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The total asymmetric synthesis of the cytotoxic marine metabolite (-)-agelastatin A (I) has been achieved from a 4,5-diamino-cyclopenten-2-one derived intermediate. This key intermediate was efficiently prepared from a sulfinimine-derived alpha-beta-diamino ester using ring closing metathesis.
PCT/US2005/041418 2004-11-16 2005-11-16 Asymmetric synthesis of (-)-agelastatin a WO2006055578A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62845604P 2004-11-16 2004-11-16
US60/628,456 2004-11-16

Publications (2)

Publication Number Publication Date
WO2006055578A2 WO2006055578A2 (en) 2006-05-26
WO2006055578A3 true WO2006055578A3 (en) 2006-07-06

Family

ID=36407698

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/041418 WO2006055578A2 (en) 2004-11-16 2005-11-16 Asymmetric synthesis of (-)-agelastatin a

Country Status (1)

Country Link
WO (1) WO2006055578A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0625783D0 (en) * 2006-12-22 2007-02-07 Univ Belfast Medicament
EP2906564B1 (en) 2012-10-12 2018-08-22 Mayo Foundation For Medical Education And Research Treating brain cancer using agelastatin a (aa) and analogues thereof
WO2014089177A2 (en) 2012-12-04 2014-06-12 Massachusetts Institute Of Technology Compounds, conjugates and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines
WO2015042239A1 (en) * 2013-09-19 2015-03-26 Massachusetts Institute Of Technology Compounds, compositions and methods of agelastatin alkaloids
EP3439659A1 (en) * 2016-04-06 2019-02-13 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods and pharmaceutical compositions for the treatment of age-related cardiometabolic diseases
US10918627B2 (en) 2016-05-11 2021-02-16 Massachusetts Institute Of Technology Convergent and enantioselective total synthesis of Communesin analogs
WO2018209239A1 (en) 2017-05-11 2018-11-15 Massachusetts Institute Of Technology Potent agelastatin derivatives as modulators for cancer invasion and metastasis
US10640508B2 (en) 2017-10-13 2020-05-05 Massachusetts Institute Of Technology Diazene directed modular synthesis of compounds with quaternary carbon centers
WO2020247054A1 (en) 2019-06-05 2020-12-10 Massachusetts Institute Of Technology Compounds, conjugates, and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines and uses thereof
CN113999241B (en) * 2021-12-09 2024-03-26 甘肃中医药大学 Method for synthesizing cephalotaxine intermediate

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANDERSON ET AL.: "Studies on Total Synthesis of the Cytotoxic Marine Alkaloid Agelastatin A", JOURNAL OF ORGANIC CHEMISTRY, vol. 63, 1998, pages 7594 - 7595 *
DOMOSTOJ ET AL.: "New Total Synthesis of the Marine Antitumor Alkaloid (-)-Agelastatin A", ORGANIC LETTERS, vol. 6, no. 5, 2004, pages 2615 - 2618 *
FELDMAN ET AL.: "Alkynliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Synthesis of (-)-Agelastatin A and (-)-Agelastatin B", JOURNAL OF ORGANIC CHEMISTRY, vol. 67, 2002, pages 7096 - 7109 *

Also Published As

Publication number Publication date
WO2006055578A2 (en) 2006-05-26

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