James John Eshelby

Model studies for the synthesis of galbonolide B

The construction of the fourteen membered ring present in galbonolide B 1 is reported. The 10,11-diene system present in the southern portion of has been constructed using an ester enolate rearrangement/silicon mediated fragmentation cascade, whilst the macrocycle has been synthesised following a Johnson rearrangement/mercury assisted ring closure protocol.

Organozinc reagents in synthesis: the facile generation of 2-(trialkylsilyl)prop-2-enylzinc from 2-bromo-1-trimethylsilylprop-2-ene

A range of electrophiles react with 2-(trimethylsilyl)prop-2-enylzinc chloride, which is prepared by sequentially treating 2-bromo-1-trimethylsilylprop-2-ene with ButLi and then zinc chloride. The addition of transition metal catalysts can alter the reactivity of the organometallic compound from prop-2-enylation to prop-1-en-2-ylation.

The construction of 1,3-dienes containing an E-double bond and an exo-methylene group

The use of a tandem Ireland Claisen rearrangement followed by an in situ silicon mediated epoxide fragmentation provides an efficient entry into 1,3-dienes containing an E-double bond and an exo-methylene group; initial results regarding remote chirality control are reported.