124655-05-6Relevant articles and documents
18O assisted analysis of a γ,δ-epoxyketone cyclization: Synthesis of the C16-C28 fragment of ammocidin D
Chau, Stephen T.,Hayakawa, Yoichi,Sulikowski, Gary A.
supporting information; experimental part, p. 756 - 759 (2011/04/24)
The C16-C28 fragment common to the cytotoxic macrolide ammocidin D has been prepared by a stereospecific 5-exo closure of a γ,δ-epoxyketone followed by a rearrangement to a pyran acetal. The reaction pathway was traced by 18O labeling of the ke
Au-catalyzed cyclization of monopropargylic triols: An expedient synthesis of monounsaturated spiroketals
Aponick, Aaron,Li, Chuan-Ying,Palmes, Jean A.
supporting information; experimental part, p. 121 - 124 (2009/07/11)
The gold-catalyzed cyclization of monopropargylic triols to form olefin-containing spiroketals is reported. The reactions are rapid and high yielding when 2 mol % of the catalyst generated in situ from Au[P(t-Bu) 2(o-biphenyl)]CI and AgOTf is e
Total synthesis of (-)-bitungolide F and determination of its absolute stereochemistry
Ghosh, Subhash,Kumar, Soma Uday,Shashidhar
, p. 1582 - 1585 (2008/09/17)
(Chemical Equation Presented) A highly convergent total synthesis of bitungolide F leading to the assignment of its absolute stereochemistry is described. The key steps include a Horner-Wadsworth-Emmons olefination to construct the C7-C8 bond, a Wittig reaction to introduce the conjugate E,E-olefinic moiety in the molecule, and finally a ring-closing metathesis reaction to construct the six-membered α,β-unsaturated δ-lactone of the molecule. Modified Evans's syn-aldol reaction, using Crimmins's protocol, was used to install the stereochemistries at the C4 and C5 centers. The stereochemistry at C9 was introduced by means of hydroxy-directed reduction of the C9 keto using Evans's protocol.
