1.
Chem Pharm Bull (Tokyo)
; 56(3): 404-6, 2008 Mar.
Article
in English
| MEDLINE
| ID: mdl-18310959
ABSTRACT
A phenylselenenyl chloride (PhSeCl)-mediated allylic oxidation to give allylically rearranged alcohol has been developed. A possible mechanism for the present reaction is generation of allylic selenide from prenyl moiety via [1,3]-sigmatropic rearrangement, followed by oxidation and [2,3]-sigmatropic rearrangement to afford 3-isopenten-2-ol.
Subject(s)
Organometallic Compounds/chemistry , Pentanols/chemical synthesis , Prenylation , Selenium/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Oxidation-Reduction
2.
Org Lett
; 9(26): 5533-6, 2007 Dec 20.
Article
in English
| MEDLINE
| ID: mdl-18027960
ABSTRACT
Stereoselective synthesis of a potential intermediate bearing 11-oxabicyclo[6.2.1]undec-3-ene core, a common scaffold of biologically active germacrane-type sesquiterpenes, has been achieved. Synthetic features involve formal 1,3-asymmetric induction, unusual ring-closing metathesis constructing a 10-membered carbocycle system, and unique lactone transposition.
