Substrate and stereocontrolled iodocycloetherification of highly functionalized enantiomerically pure allylic alcohols: application to synthesis of cytotoxic 2-epi jaspine B and its biological evaluation.

Abstract

Stereoselectivities of electrophilic additions of molecular iodine to enantiomerically pure highly functionalized allylic alcohols with internal nucleophiles have been investigated. The intramolecular nucleophilic attack on the I2-π complex by an oxygen nucleophile to obtain tri- and tetrasubstituted THFs is highly regio-, stereoselective and substrate controlled. The application of this study has been shown by utilizing one of the THFs 4a as a key intermediate to complete the total synthesis of marine anti-cancer natural product 2-epi jaspine B.

• Authors: Somireddy Kundooru, Pintu Das, Sanjeev Meena, Vikash Kumar, Mohammad Imran Siddiqi, Dipak Datta, Arun K Shaw
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 13 Issue 30 Pg. 8241-50 (Aug 14 2015) ISSN: 1477-0539 [Electronic] England
• PMID: 26133669 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Ethers
• Iodides
• Propanols
• pachastrissamine
• allyl alcohol
• Sphingosine

Topics

• Cell Death (drug effects)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cyclization
• Ethers (chemistry)
• Humans
• Inhibitory Concentration 50
• Iodides (chemistry)
• Magnetic Resonance Spectroscopy
• Molecular Conformation
• Propanols (chemistry)
• Sphingosine (analogs & derivatives, chemical synthesis, chemistry, pharmacology, toxicity)
• Stereoisomerism