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Studies Toward the Total Synthesis of Cerorubenic Acid-III
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Abstract
Discussion Points What is the purpose of FeCl3 in step d? Give reasons for the high stereoselectivity observed in nucleophilic additions to the cyclopropane-containing system (e.g. step f). When the Wittig/ Grignard addition sequence was carried out in the inverse order, compound 10 was isolated instead. How can this result be explained? Explain the stereoselectivity and the complete regioselectivity observed in the Diels-Alder reaction of step n. Further Reading For further studies towards cerorubenic acid-III, see: L.A. Paquette, S. Hormuth and C. J. Lovely, J. Org. Chem., 1995, 60, 4813; L.A. Paquette, G. Y. Lassalle and C. J. Lovely, J. Org. Chem.,1993, 58,4254; L.A. Paquette, D. N. Deaton, Y. Endo and M.-A. Poupart, J. Org. Chem.,1993, 58,4262. For a review on anion-assisted sigmatropic rearrangements, see: S. R. Wilson, Org. React.,1993, 43,93. For reviews on the oxy-Cope rearrangement, see: K. Durairaj, Curr. Sci., 1994, 66,917; L.A. Paquette, Synlett.,1990, 2,67. For another application of oxidative dianion coupling in natural product synthesis, see: J. L. Belletire and D. F. Fry, J. Org. Chem.,1988, 53,4724. For a review on the enhancement of rate and selectivity in Diels-Alder reactions, see: U. Pindur, G. Lutz and C. Ott, Chem. Rev.,1993, 93,741.
Oxford University PressOxford
Title: Studies Toward the Total Synthesis of Cerorubenic Acid-III
Description:
Abstract
Discussion Points What is the purpose of FeCl3 in step d? Give reasons for the high stereoselectivity observed in nucleophilic additions to the cyclopropane-containing system (e.
g.
step f).
When the Wittig/ Grignard addition sequence was carried out in the inverse order, compound 10 was isolated instead.
How can this result be explained? Explain the stereoselectivity and the complete regioselectivity observed in the Diels-Alder reaction of step n.
Further Reading For further studies towards cerorubenic acid-III, see: L.
A.
Paquette, S.
Hormuth and C.
J.
Lovely, J.
Org.
Chem.
, 1995, 60, 4813; L.
A.
Paquette, G.
Y.
Lassalle and C.
J.
Lovely, J.
Org.
Chem.
,1993, 58,4254; L.
A.
Paquette, D.
N.
Deaton, Y.
Endo and M.
-A.
Poupart, J.
Org.
Chem.
,1993, 58,4262.
For a review on anion-assisted sigmatropic rearrangements, see: S.
R.
Wilson, Org.
React.
,1993, 43,93.
For reviews on the oxy-Cope rearrangement, see: K.
Durairaj, Curr.
Sci.
, 1994, 66,917; L.
A.
Paquette, Synlett.
,1990, 2,67.
For another application of oxidative dianion coupling in natural product synthesis, see: J.
L.
Belletire and D.
F.
Fry, J.
Org.
Chem.
,1988, 53,4724.
For a review on the enhancement of rate and selectivity in Diels-Alder reactions, see: U.
Pindur, G.
Lutz and C.
Ott, Chem.
Rev.
,1993, 93,741.
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