7
2. Synthetic Utilization of pentafulvenes

2. Synthetic Utilization of pentafulvenes

  • Upload
    devi

  • View
    30

  • Download
    2

Embed Size (px)

DESCRIPTION

2. Synthetic Utilization of pentafulvenes. NIIST. 2. Development of Synthetic Methodologies towards Fused Cyclooctanoids. Some of the Biologically active cyclooctanoids. Developed a Novel Methodology for the synthesis of 5-8 fused Cyclooctanoids. Tet. Lett . 2005, 46, 4785-4788. NIIST. - PowerPoint PPT Presentation

Citation preview

Page 1: 2. Synthetic Utilization of pentafulvenes

2. Synthetic Utilization of pentafulvenes

Page 2: 2. Synthetic Utilization of pentafulvenes

2. Development of Synthetic Methodologies towards Fused Cyclooctanoids2. Development of Synthetic Methodologies towards Fused CyclooctanoidsNIIST

OH

H OH

OHHO

HO

H

H

H

OHOH

Dactylol Kalmanol

OO

O

H

Asteriscanolide

H

OO

O

O

O

HO H

HO

O

HH

O

OH

Anti-HIV activeLancifodilactone G

H

Some of the Biologically active cyclooctanoidsSome of the Biologically active cyclooctanoids

O

O

AcO Et3N

CHCl3

R1R

O

O

R1R

O

O

[6+3]

Developed a Novel Methodology for the synthesis of 5-8 fused CyclooctanoidsDeveloped a Novel Methodology for the synthesis of 5-8 fused Cyclooctanoids

Tet. LettTet. Lett. 2005, 46, 4785-4788

Page 3: 2. Synthetic Utilization of pentafulvenes

O

O

N Bn

N Bn

O

O

N

O

O

Ph

O

O

AcO R2

TFA

Et3N

O

ON

O

O

Ph

H

H

H

Toluene, RT

O

O

O

O

OO

OO

R2

R1R1

R2

Syn-anti Syn-syn

Utilization of the Developed Synthetic MethodologyNIIST

Tet. LettTet. Lett. 2005, 46, 4785-4788

TetrahedronTetrahedron, 2006, 5952-5961

Tetrahedron,Tetrahedron, 2006, 62, 12345;

SynthesisSynthesis, 2006,11, 1811-1818

Eur. J. Org. Chem. Eur. J. Org. Chem. 2007, 5847, 5847

Page 4: 2. Synthetic Utilization of pentafulvenes

O

OOH

H

O

H

H

O

O

O OR

RuCl3.3H2O

H2

O

O

R

O

O

R

O

O

AcO

NaIO4

O

O

O

i. CPD, base

ii.

Pd/C

Neodolabellane

R

Novel route to eleven membered rings and spirocyclic cyclooctanoidsNovel route to eleven membered rings and spirocyclic cyclooctanoidsNIIST

“Heterocycles via Pyrylium and Pyridinium Betaines”,”, K. V. Radhakrishnan,

Topics in Heterocyclic Chemistry, Vol. Synthesis of Heterocycles via Cycloadditions, 13, 2008,

pages-71-98., Springer.

Eur. J. Org. ChemEur. J. Org. Chem. .

2007, 5847, 5847

Synthesis, 2008, 13, 2134

Page 5: 2. Synthetic Utilization of pentafulvenes

O

Br

R-OH

OBz

O

O

O

Ph

OR

BzO

2,6-Lutidine

[bmim]PF6

N

N

H3C

PF6

[bmim]PF6

NIIST

3. Synthetic Carbohydrate Chemistry

1,2-Orthoesters- Important Intermediates in Synthetic Carbohydrate Chemistry

For eg: n-Pentenyl Orthoesters as Glycoside Donors

Design, Synthesis and Host-Guest Evaluation of NeoglycoconjugatesDesign, Synthesis and Host-Guest Evaluation of Neoglycoconjugates

Ionic liquid [bmim]PFIonic liquid [bmim]PF66 Mediated Synthesis of 1,2-Orthoesters of Carbohydrates Mediated Synthesis of 1,2-Orthoesters of Carbohydrates

We have developed a facile and environmentally benign method for the We have developed a facile and environmentally benign method for the

synthesis of 1,2- orthoesters of carbohydrates and Glycosidation reactions ofsynthesis of 1,2- orthoesters of carbohydrates and Glycosidation reactions of

NPOE in ionic liquid [bmim]PFNPOE in ionic liquid [bmim]PF66..

The method is much simpler and the solvent can be reused several timesThe method is much simpler and the solvent can be reused several times

Synlett, 2005, 6, 997Bull. Chem. Soc. Jpn. 2007, 553.

Page 6: 2. Synthetic Utilization of pentafulvenes

Synthesis and Study of Carbohydrate Appended Mutivalent ligands

Synthesis of higher order glycoconjugates as

probes to define the molecular nature of

carbohydrate-receptor interactions

Interaction of metal ions with carbohydrates is an important element for

biochemical processes

Metal complexes involving carbohydrates clarify many functions of

carbohydrates in natural systems

Carbohydrates as Scaffolds by attaching

a chelating ligand for cation and anion binding

Page 7: 2. Synthetic Utilization of pentafulvenes

Able to encapsulate guest molecules

Synthesis and study of Carbohydrate-coated Nanocapsules

Target selective nanocarriers

Labelling specific protein

Sensing of a range of pathogens.

Vesicles

Nanorods

NIIST Photochromic nanocapsules Multivalent nanoscaffolds for selective

interactions