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Total Synthesis Of Bio-Active Natural Products Microcarpalide, Synargentolide A, Jaspine B And Anamarine

Electronic Theses of Indian Institute of Science

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Title Total Synthesis Of Bio-Active Natural Products Microcarpalide, Synargentolide A, Jaspine B And Anamarine
 
Creator Penchalaiah, Kamala
 
Subject Organics Synthesis
Microcarpalide
Synargentolide
Jaspine B
Chiral Building Blocks
Anamarine
Pachastrissamine
Hydroxy Cyclopentenone
Organic Chemistry
 
Description The thesis entitled “Total synthesis of bio-active natural products microcarpalide, synargentolide A, jaspine B and anamarine.” demonstrates the utility of chiral pool tartaric acid as the source in the synthesis of bio-active natural products. The thesis was divided into four sections.
Section I of the thesis deals with the enantiodivergent synthesis of microcarpalide from tartaric acid. Microcarpalide is a 10-membered lactone of polyketide origin isolated from the fermentation broths of an unidentified endophytic fungi, found to be weekly cytotoxic to mammalian cells and acts as a microfilament discrupting agent. Stereoselective approach for the synthesis of ()-microcarpalide is described from D- and L-tartaric acids, while enantiodivergent approach for the synthesis of both enantiomers is described from L-tartaric acid using ring closing metathesis as the
Scheme 2: Enantiodivergent total synthesis of microcarpalide.
In section II of the thesis, stereoselective synthesis of synargentolide A is described. Synargentolide A is a polyhydroxy -lactone, isolated from Syncolostemon argenteus, which was founf to exhibit cytotoxic and antitumor properties. Stereoselective synthesis of synargentolide A was accomplished, starting from L-tartaric acid employing, Keck and Brown allylations and ring closing metathesis, as the key steps.
Scheme 3: Stereoselective total synthesis of ()-synargentolide A.
Section III of the thesis deals with the synthesis of ()-jaspine B. Pachastrissamine (jaspine B), is an anhydrophytoshingosine derivative, isolated from marine sponges Pachastrissa and Jaspis speces. Pachastrissamine was shown to exhibit cytotoxicity (IC 50 0.01 g/mL) against P388, A549, HT29, and MEL28 cell lines. Enantioselective synthesis of jaspine B is accomplished from L-tartaric acid employing, Keck allylation, acid mediated formation of tetrahydrofuran, and olefin cross metathesis as the key reactions.
In section IV of the thesis, enantioselective synthesis of ()-anamarine is described. Anamarine is a polyhydroxy -lactone isolated from the flowers and leaves of Peruvian hyptis, possessing cytotoxicity against human tumor cell lines. Enantioselective synthesis of -anamarine is accomplishedelaboration of hitherto unknown -keto phosphonate derived from tartaric acid amide.
In an appendix for the thesis, enantiodivergent synthesis for 4-siloxy-pent-2-enone was described. The usefulness of asymmetric aldol reaction is exemplifiedin this section. hydroxy amide synthesized from crotonaldehyde is suitably elaborated to the diene which on RCM yielded 4-silyloxycyclopent-2-enone. Further synthetic modification of this compound afforded the other enantiomer.
Scheme 6: Enantiodivergent synthesis of hydroxy cyclopentenones.
(For structural formula pl the abstract pdf file)
 
Contributor Prasad, Kavirayani R
 
Date 2013-05-23T10:29:51Z
2013-05-23T10:29:51Z
2013-05-23
2011-08
 
Type Thesis
 
Identifier http://etd.iisc.ernet.in/handle/2005/2007
http://etd.ncsi.iisc.ernet.in/abstracts/2597/G24987-Abs.pdf
 
Language en_US
 
Relation G24987