- A concise, stereocontrolled total synthesis of rippertenol
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The first total synthesis of the unique terpene rippertenol, a molecule with dense stereochemical complexity arrayed on a compact framework largely devoid of functional groups, is described. Key elements include orchestrated and unique applications of aldol condensations, Diels-Alder chemistry, and a ring expansion to advance a chiral starting material containing a single chiral center into the final target in a concise and diastereocontrolled manner.
- Snyder, Scott A.,Wespe, Daniel A.,Von Hof, J. Marian
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- Concise total syntheses of the sesquiterpenoids (-)-homalomenol A and (-)-homalomenol B
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The conjugate additions of the organocopper(I) reagents 22 and 27 to the enantiomerically homogeneous bicyclic enone 4 provided, after epimerization (NaOMe, MeOH) of the resultant product mixtures and appropriate chromatographic separations, the bicyclo[4.3.0]nonan-2-ones 24 and 28. Compounds 24 and 28 were readily converted, via two synthetic steps in each case, into the sesquiterpenoids (-)-homalomenols B (2) and A (1), respectively.
- Piers, Edward,Oballa, Renata M.
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p. 8439 - 8447
(2007/10/03)
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- Synthesis of optically active cyclohexenol derivatives via enzyme catalyzed ester hydrolysis of 4-acetoxy-3-methyl-2-cyclohexenone
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The optically active cyclohexenol derivatives 9a-9d, and 10a-10c are synthesized from (-)-6, which is obtained by enzymatic ester hydrolysis of racemic 8. Attempts towards the synthesis of the taxane skeleton are described.
- Polla, Magnus,Frejd, Torbjoern
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p. 5883 - 5894
(2007/10/02)
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