848731-59-9Relevant academic research and scientific papers
Total synthesis of (-)-sarain A
Becker, Michael H.,Chua, Peter,Downham, Robert,Douglas, Christopher J.,Garg, Neil K.,Hiebert, Sheldon,Jaroch, Stefan,Matsuoka, Richard T.,Middleton, Joy A.,Ng, Fay W.,Overman, Larry E.
, p. 11987 - 12002 (2008/04/04)
This article describes the details of our synthetic studies toward the complex marine alkaloid sarain A. Various strategies were conceived, setbacks encountered, and solutions developed, ultimately leading to a successful enantioselective total synthesis. Our route to (-)-sarain A features a number of key steps, including an asymmetric Michael addition to install the C4′-C3′-C7′ stereotriad, an enoxysilane-N-sulfonyliminium ion cyclization to set the C3 quaternary carbon stereocenter, and assemble the diazatricycloundecane core, a ring-closing metathesis to construct the 13-membered ring, an intramolecular Stille coupling to fashion the unsaturated 14-membered macrocycle, and a late-stage installation of the tertiary amine-aldehyde proximity interaction.
Total synthesis of (-)-sarain A
Garg, Neil K.,Hiebert, Sheldon,Overman, Larry E.
, p. 2912 - 2915 (2007/10/03)
The final synthetic challenges associated with sarain A have been overcome, thus leading to its first total synthesis. Critical to success was a late-stage intramolecular Stille coupling to construct the unsaturated macrocyclic ring and introduce the skip
Toward an enantioselective total synthesis of sarain A: Construction of an advanced intermediate and rearrangement of the sarain A core under mild conditions
Douglas, Christopher J.,Hiebert, Sheldon,Overman, Larry E.
, p. 933 - 936 (2007/10/03)
(Chemical Equation Presented) A high-yielding N-sulfonyliminium ion-enoxysilane cyclization and a ring-closing metathesis are key steps in the enantioselective synthesis of late-stage intermediates en route to sarain A. Also revealed is an unprecedented rearrangement of the tetracyclic sarain A core under mildly acidic conditions.
