329366-69-0Relevant articles and documents
A formal synthesis of herboxidiene/GEX1A
Yadav, Jhillu S.,Reddy, G. Madhusudhan,Anjum, S. Rehana,Reddy, B. V. Subba
, p. 4389 - 4397 (2014/07/21)
A formal synthesis of herboxidiene/GEX 1A is described. This approach demonstrates successful application of the Prins cyclization for the construction of the tetrahydropyran core of the target molecule. The chirality of the side chain has been established through the Sharpless asymmetric dihydroxylation and Evan's alkylation. The olefin cross-metathesis was applied to couple both key fragments. Copyright
A total synthesis of herboxidiene methyl ester
Premraj, Rajaratnam,McLeod, Malcolm D.,Simpson, Gregory W.,Banwell, Martin G.
, p. 2949 - 2976 (2013/02/21)
The total synthesis of the methyl ester, 35, of herboxidiene (1, a.k.a. GEX1A and TAN-1609), a polyketide displaying both herbicidal and anti-tumor activity, is described. The convergent reaction sequence involves, in its closing stages, the union of the phosphine oxide 3 with the aldehyde 21 to deliver, via a Horner-Wittig reaction with accompanying epimerization at C12, compound 33 that after deprotection affords an alcohol, 34, capable of participating in a regioand diastereo-selective epoxidation reaction to give target 35. Phosphine oxide 3 was prepared via the intramolecular hetero-Michael addition of a secondary alcohol to a tethered and Z-configured acrylate while aldehyde 21 was generated, in the crucial step of the relevant reaction sequence, via an Ireland-Claisen rearrangement reaction.
