164364-99-2Relevant articles and documents
Total synthesis of (+)-asteltoxin
Eom, Khee Dong,Raman, J. Venkat,Kim, Heejin,Cha, Jin Kun
, p. 5415 - 5421 (2007/10/03)
A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner-Emmons olefination of bis(tetrahydrofuran) aldehyde 53 and α-pyrone phosphonate 5. A key step features the stereoselective construction of a sterically congested quaternary center embedded in the densely functionalized bis(tetrahydrofuran) subunit by a Lewis acid-catalyzed, pinacol-type rearrangement of an epoxy silyl ether. This pivotal rearrangement methodology parallels the proposed biosynthetic pathway of 1 and is ripe for applications to the stereocontrolled synthesis of structurally complex natural products.