[go: up one dir, main page]

Nicolaou et al., 1993 - Google Patents

Total synthesis of calicheamicin. gamma. 1I. 3. The final stages

Nicolaou et al., 1993

Document ID
15265189341794393644
Author
Nicolaou K
Hummel C
Nakada M
Shibayama K
Pitsinos E
Saimoto H
Mizuno Y
Baldenius K
Smith A
Publication year
Publication venue
Journal of the American Chemical Society

External Links

Snippet

The first total synthesis of calicheamicin 711 (1) has been achieved. The stereoselective glycosidation, joining the appropriately functionalized aglycon 3 with the oligosaccharide fragment 2, was realized using Schmidt's trichloroacetimidate methodology. Segment 4 …
Continue reading at pubs.acs.org (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C-Si linkages
    • C07F7/18—Compounds having one or more C-Si linkages as well as one or more C-O-Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1812—Compounds having Si-O-C linkages having (C1)a-Si-(OC2)b linkages, a and b each being >=1 and a+b = 4, C1 and C2 being hydrocarbon or substituted hydrocarbon radicals
    • C07F7/1844—Compounds having Si-O-C linkages having (C1)a-Si-(OC2)b linkages, a and b each being >=1 and a+b = 4, C1 and C2 being hydrocarbon or substituted hydrocarbon radicals a being 3, b being 1
    • C07F7/1848—C1 being an unsubstituted acyclic saturated hydrocarbon radical containing less than six carbon atoms, a benzyl radical, a phenyl radical, or a methyl substituted phenyl radical
    • C07F7/1856—C2 containing cycloaliphatic, heterocyclic or condensed aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0042—Nitrogen only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00

Similar Documents

Publication Publication Date Title
Nicolaou et al. Total synthesis of calicheamicin. gamma. 1I. 3. The final stages
Groneberg et al. Total synthesis of calicheamicin. gamma. 1I. 1. Synthesis of the oligosaccharide fragment
US5384412A (en) Saccharide intermediates in the formation of the calicheamicin and esperamicin oligosaccharides
US5264586A (en) Analogs of calicheamicin gamma1I, method of making and using the same
JP6216417B2 (en) 9,10-α, α-OH-taxane analogs and methods for their production
AU691575B2 (en) Delta 12,13--iso-taxol analogs, antineoplastic use and pharmaceutical compositions containing them
SI9011699A (en) Heterocyclic compounds
CA2894536A1 (en) Mannose derivatives for treating bacterial infections
CA2020072A1 (en) Synthetic process for fk-506 type macrolide intermediates
JP2000109497A (en) Spiro ring type c-glycoside
JP2001521037A (en) Sarcodicin and eleuserobin useful for microtubule stabilization
UA63956C2 (en) A method for preparing thiazofurine and other c-nucleosides
CA2146548A1 (en) Antineoplastic heteronaphthoquinones
US4267113A (en) Antitumor agents
EP0349676A1 (en) Tylosin derivatives and process for producing the same
Jurczak et al. The total synthesis of l-daunosamine
CZ185193A3 (en) Heterocyclic derivatives, process of their preparation and pharmaceutical preparations in which they are comprised
US5606037A (en) Processes antineoplastic heteronaphthoquinones
US5736523A (en) Antineoplastic heteronapthoquinones
Tronchet et al. Synthesis of pyrazole C-glycosides by 1, 3-dipolar cycloaddition of nitrilimines formed by lead tetraacetate oxidation of p-nitrophenylhydrazones of aldehydo sugars
EP0454494A2 (en) Calicheamicinone, derivatives and analogs thereof and methods of making the same
US4433158A (en) 3-Hydroxyiminoscirpen-4β, 15-diol esters useful as antitumor agents
WO1995008553A1 (en) Synthesis of selectin ligands
Follows Studies directed toward the synthesis of the calicheamicin ABE core trisaccharide
Smith The design, synthesis and DNA-binding properties of complex carbohydrates