Diastereoselective formal total synthesis of the DNA polymerase alpha inhibitor, aphidicolin, using palladium-catalyzed cycloalkenylation and intramolecular Diels-Alder reactions

Masahiro Toyota; Masato Sasaki; Masataka Ihara

doi:10.1021/ol034027+

Diastereoselective formal total synthesis of the DNA polymerase alpha inhibitor, aphidicolin, using palladium-catalyzed cycloalkenylation and intramolecular Diels-Alder reactions

Org Lett. 2003 Apr 17;5(8):1193-5. doi: 10.1021/ol034027+.

Authors

Masahiro Toyota¹, Masato Sasaki, Masataka Ihara

Affiliation

¹ Department of Organic Chemistry, Graduate School of Pharmaceutical Science, Tohoku University, Aobayama, Sendai 980-8578, Japan. mihara@mail.pharm.tohoku.ac.jp

PMID: 12688717
DOI: 10.1021/ol034027+

Abstract

[structure: see text] A novel diastereoselective formal synthesis of aphidicolin has been achieved by exploiting a unique characteristic of a bicyclo[3.2.1]octane prepared by employing a palladium-catalyzed cycloalkenylation process.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aphidicolin / chemical synthesis*
Aphidicolin / pharmacology
Catalysis
Cyclization
DNA Polymerase I / antagonists & inhibitors*
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / pharmacology
Octanes / chemistry
Organometallic Compounds / chemistry*
Palladium / chemistry*
Stereoisomerism

Substances

Enzyme Inhibitors
Octanes
Organometallic Compounds
Aphidicolin
Palladium
DNA Polymerase I
octane