Bioinspired Total Synthesis of Gymnothelignan N

Bioinspired total synthesis of (±)-yezo'otogirin C.

The first and protective group-free total synthesis of (±)-yezo'otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo'otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxi...

Bioinspired Total Synthesis of Bussealin E.

The first total synthesis of bussealin E, a natural product with a unique cycloheptadibenzofuran scaffold, is reported. A strategy inspired by a proposed biosynthesis was employed whereby a diphenylpropane derivative underwent an oxidative phenolic coupling to forge the tetracyclic ring system. The synthesis of the diphenylpropane featured a key sp2-sp3 Hiyama coupling between a vinyldisiloxane...

Total synthesis of (-)-calyciphylline N.

The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenati...

Bioinspired Synthesis of Magnetic Nanoparticles

Bioinspired iterative synthesis of polyketides

Diverse array of biopolymers and second metabolites (particularly polyketide natural products) has been manufactured in nature through an enzymatic iterative assembly of simple building blocks. Inspired by this strategy, molecules with inherent modularity can be efficiently synthesized by repeated succession of similar reaction sequences. This privileged strategy has been widely adopted in synt...