696592-76-4Relevant academic research and scientific papers
Conformational biasing in 1,3-oxidative rearrangements of dienols
Majetich, George,Nishide, Hisaya,Phillips, Ryan M.,Yu, Jianhua
, p. 225 - 231 (2008/09/17)
1-Vinyl-2-cycloalkenols are oxidized to form conjugated dienones in useful yields. Although this oxidative rearrangement is general, severe steric interactions can favor the formation of a conjugated dienal instead of a conjugated dienone. Several heteroc
Efficient formal synthesis of (±)-hyphodermin B
Henderson, Luke C.,Loughlin, Wendy A.,Jenkins, Ian D.,Healy, Peter C.,Campitelli, Marc R.
, p. 2384 - 2388 (2007/10/03)
An efficient formal synthesis of hyphodermin B 1, a metabolite of Hyphoderma radula, has been completed in 15% overall yield. The tricyclic carbon skeleton 3 was rapidly assembled from a novel vinyl enone via a Diels-Alder reaction, followed by dehydrogen
Lipase-catalyzed domino dynamic kinetic resolution of racemic 3-vinylcyclohex-2-en-1-ols/intramolecular diels-alder reaction: One-pot synthesis of optically active polysubstituted decalins
Akai, Shuji,Tanimoto, Kouichi,Kita, Yasuyuki
, p. 1407 - 1410 (2007/10/03)
Combining chemistry: The use of a lipase and a ruthenium catalyst allows the direct preparation of polysubstituted decalines with high optical and chemical yields from racemic alcohols (see scheme). The lipase-catalyzed kinetic resolution of the racemic alcohols, the ruthenium-catalyzed racemization of the slow-reacting enantiomers, and an intramolecular Diels-Alder reaction of the resultant esters all occur under identical conditions.
Total synthesis of natural dysidiolide
Miyaoka,Kajiwara,Hara,Yamada
, p. 1429 - 1435 (2007/10/03)
Dysidiolide (1), a novel sesterterpenoid previously isolated from the Caribbean sponge Dysidea etheria de Laubenfels, inhibits the action of the protein phosphatase, cdc25A. The authors establish a novel total synthesis of natural dysidiolide (1) using intramolecular Diels - Alder reaction as the key step from optically active cyclohexenone 3. Decalin, the core structure of 1, was constructed by intramolecular Diels - Alder reaction of the diene ester generated by elimination of the phenyl sulfoxide group from sulfoxide ester 6 prepared from cyclohexenone 3. Diastereoselective methylation at C-7, alkylation at C-6, and deoxygenation of C-12 and C-24 positions gave the fully substituted bicyclic core of 1. The two side chains of the bicyclic core were further extended so as to afford natural dysidiolide (1). The total yield of this synthesis exceeds that of previous syntheses of 1.
