860438-73-9Relevant articles and documents
4-(Phenylsulfonyl)-4-lithiocyclopentene as a nucleophilic 2-pentene-1,5-dial synthetic equivalent. An aziridine-based synthetic approach to (-)-alstonerine
Cox, Paul,Craig, Donald,Ioannidis, Stephanos,Rahn, Volker S.
, p. 4687 - 4690 (2005)
Reaction of 4-lithio-4-(phenylsulfonyl)cyclopentene with an l-tryptophan-derived N-tosylaziridine provides an adduct. Oxidative cleavage of the cyclopentene double bond provides a dialdehyde, which enters into acid-catalysed Pictet-Spengler-type bicyclisation to give a tetracyclic aldehyde. Completely regioselective silyl dienol ether formation followed by completely stereoselective hetero-Diels-Alder reaction with monomeric formaldehyde gives a late-stage intermediate in a planned total synthesis of the macroline-related alkaloid (-)-alstonerine.