686718-85-4Relevant articles and documents
An improved synthesis of the scyphostatin side-chain
McAllister, Graeme D.,Taylor, Richard J. K.
, p. 2551 - 2554 (2004)
A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling.
Total synthesis of (+)-scyphostatin, a potent and specific inhibitor of neutral sphingomyelinase
Inoue, Munenori,Yokota, Wakako,Murugesh, Modachur G.,Izuhara, Takashi,Katoh, Tadashi
, p. 4207 - 4209 (2007/10/03)
The five crucial steps in the first total synthesis of (+)-scyphostatin from D-arabinose involve (see picture): a) stereoselective aldol coupling to form a quaternary stereocenter, b) ring-closing metathesis (RCM) to construct the cyclohexene ring, c) Neg