Total Syntheses of (±)-Preussomerins G and I
- 17 May 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (1) , 3-6
- https://doi.org/10.1021/ol990020+
Abstract
Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.Keywords
This publication has 13 references indexed in Scilit:
- Syntheses of palmarumycin CP1 and CP2, CJ-12,371 and novel analoguesTetrahedron Letters, 1998
- Absolute stereochemistry of the diepoxinsTetrahedron, 1996
- Cladospirone bisepoxide: Definite structure assignment including absolute configuration and selective chemical transformationsTetrahedron, 1995
- CJ-12,371 and CJ-12,372, Two Novel DNA Gyrase Inhibitors. Fermentation, Isolation, Structural Elucidation and Biological Activities.The Journal of Antibiotics, 1995
- Cladospirone bisepoxide - a novel fungal metabolite structure determinationTetrahedron Letters, 1994
- Diepoxins, novel fungal metabolites with antibiotic activityTetrahedron Letters, 1993
- Structures of nostocyclophanes A-DThe Journal of Organic Chemistry, 1991
- Structure of preussomerin A: an unusual new antifungal metabolite from the coprophilous fungus Preussia isomeraJournal of the American Chemical Society, 1990
- A regiospecific synthesis of functionalized vinylcyclopropanes via cyclopropyl cupratesThe Journal of Organic Chemistry, 1976
- Indoaniline Dyes. V.1 Some Dyes Derived from Substituted α-NaphtholsJournal of the American Chemical Society, 1961