34673-07-9Relevant academic research and scientific papers
A modular and concise total synthesis of (±)-daurichromenic acid and analogues
Hu, Hongjuan,Harrison, Tyler J.,Wilson, Peter D.
, p. 3782 - 3786 (2004)
A modular and concise total synthesis of (±)-daurichromenic acid has been accomplished in four steps from ethyl acetoacetate, ethyl crotonate, and trans,trans-farnesal. A series of analogues of this natural product, which has potent anti-HIV activity, were also prepared from ethyl or methyl acetoacetate and a series of readily available α,β-unsaturated esters and aldehydes.
Total synthesis of (±)-dysidiolide
Demeke, Damtew,Forsyth, Craig J
, p. 6531 - 6544 (2007/10/03)
The total synthesis of (±)-dysidiolide was accomplished with a high level of intramolecular stereo-induction. Methylation of 6-carboethoxy-3-chloro-5-methyl-cyclohex-2-enone provided 33 bearing the 6,7-trans-dimethyl substitution of the C6-C11 B-ring. Diastereoselective conjugate addition upon enone 34 installed the C11 stereogenic center. Annulation then provided an A-ring enone (23), a substrate for a challenging conjugate addition of the branched pentenyl side chain. The combination of tri-n-butylphosphine, boron trifluoride etherate, and a dialkylcuprate uniquely effected conjugate addition to yield 58. Incorporation of the hydroxybutenolide-containing side chain completed the total synthesis and established the viability of a general approach for the preparation of the isolabdanoid terpene system.
