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Synthesis Of Bioactive Marine Meroterpenoids : Frondosins And Liphagal

Electronic Theses of Indian Institute of Science

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Field Value
 
Title Synthesis Of Bioactive Marine Meroterpenoids : Frondosins And Liphagal
 
Creator Shripad, Likhite Nachiket
 
Subject Biosynthesis
Terpenoids - Synthesis
Meroterpenoids
Frondosins
Liphagal
Marine Natural Products - Synthesis
Meroterpenoid
Organic Chemistry
 
Description The sea conceals a mermaid’s grotto of useful chemicals-marine natural products of therapeutic potential. Marine sponges in particular are a rich source of natural products with structural diversity and novel biological activity. In recent times, there has been a growing interest in the synthesis of marine natural products. The present thesis entitled, “Synthesis of bioactive marine meroterpenoids: frondosins and liphagal” is an endeavor along the same lines and is organized under two parts –Part A and Part B.
Part A: Studies towards the total synthesis of (±) frondosins A and B
Frondosins A-E are IL-8 inhibiting marine meroterpenoids, with novel bicyclo[5.4.0]undecane framework, exhibiting anti-inflammatory and anti HIV-1 activities. A relatively simple and inherently flexible ring-closing metathesis (RCM) based strategy was employed to achieve the total synthesis of frondosins A (formal) and B in only 17 linear steps (total 13 operations) and 5% overall yield. A concise route, based on RCM, to the core structure of bioactive frondosins is amenable to ready appendage diversification and enables implementation of functionalization manoeuvres on all positions in the seven-membered ring of the bicyclic framework was also developed. A Diels-Alder strategy that led to the synthesis of 8-des-methyl norfrondosin A dimethyl ether is also delineated in Part A of the thesis.
Part B: A concise synthesis of (±) liphagal
Liphagal is a marine meroterpenoid displaying an unprecedented “liphagane” skeleton. It is a selective inhibitor of PI3K  and significantly toxic against a small panel of human tumor cell lines (LoVo, CaCo-human colon and MDA-468-human breast). A concise and straightforward biomimetic strategy towards liphagal and its 14-des-formyl analogue that awarded liphagal dimethyl ether in only eight steps from commercially available building blocks is described in Part B of the thesis.
 
Contributor Mehta, Goverdhan
 
Date 2013-05-20T09:52:05Z
2013-05-20T09:52:05Z
2013-05-20
2009-10
 
Type Thesis
 
Identifier http://etd.iisc.ernet.in/handle/2005/1993
http://etd.ncsi.iisc.ernet.in/abstracts/2581/G23511-Abs.pdf
 
Language en_US
 
Relation G23511