Combining the [2,3] sigmatropic rearrangement and ring-closing metathesis strategies for the synthesis of spirocyclic alkaloids. A short and efficient route to (±)-perhydrohistrionicotoxin

Tetrahedron

Volumn 55, Issue 5, 1999, Pages 1427-1440

  Tanner, David ^a   Hagberg, Lars ^a,b   Poulsen, Anders ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

Alkaloids; Metathesis; Rearrangements; Spiro compounds

Indexed keywords

ALKALOID; PERHYDROHISTRIONICOTOXIN; RUTHENIUM; SELENIUM;

ARTICLE; CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033613804     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01115-6     Document Type: Article

References (50)

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34. Cvetovich, R. J. Diss. Abstr. Int. B. 1979, 39(8) 3837. (Chemical Abstracts 1979, 90, 186758q.) The work described in this dissertation was performed in the laboratory of Prof. Gilbert Stork at Columbia University. The thesis describes a total synthesis of (±)-depentylperhydrohistrionicotoxin which is similar to the present work in that it starts from 2,3-epoxycyclohexan-1-one and involves a [2,3] sigmatropic rearrangement (based, however, on sulfur) to set up the spirocyclic centre. A lucid analysis of the stereochemical features of the sigmatropic rearrangement is presented, along with a clever stratagem for control of diastereofacial selectivity in that step, via the ketal shown below. Subsequent elaboration of the spirocycle requires 6 steps and conversion of the ketal to the butyl side-chain 3 steps. The total synthesis requires ca. 18 steps and proceeds in ca. 3% overall yield. (equation presented)
35. Cvetovich, R. J. Diss. Abstr. Int. B. 1979, 39(8) 3837. (Chemical Abstracts 1979, 90, 186758q.) The work described in this dissertation was performed in the laboratory of Prof. Gilbert Stork at Columbia University. The thesis describes a total synthesis of (±)-depentylperhydrohistrionicotoxin which is similar to the present work in that it starts from 2,3-epoxycyclohexan-1-one and involves a [2,3] sigmatropic rearrangement (based, however, on sulfur) to set up the spirocyclic centre. A lucid analysis of the stereochemical features of the sigmatropic rearrangement is presented, along with a clever stratagem for control of diastereofacial selectivity in that step, via the ketal shown below. Subsequent elaboration of the spirocycle requires 6 steps and conversion of the ketal to the butyl side-chain 3 steps. The total synthesis requires ca. 18 steps and proceeds in ca. 3% overall yield. (equation presented)
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44. Computational studies were performed with the MacroModel V6.0 program (Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440) using force field MMFF as implemented in MacroModel (Halgren, T. A. J. Comput. Chem. 1996, 17, 490; 520; 553; 587; 616) and conformational searches were performed with the Monte Carlo routine (Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110). We thank Dr. P. O. Norrby for help and advice regarding the computational studies.
45. Computational studies were performed with the MacroModel V6.0 program (Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440) using force field MMFF as implemented in MacroModel (Halgren, T. A. J. Comput. Chem. 1996, 17, 490; 520; 553; 587; 616) and conformational searches were performed with the Monte Carlo routine (Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110). We thank Dr. P. O. Norrby for help and advice regarding the computational studies.
46. Computational studies were performed with the MacroModel V6.0 program (Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440) using force field MMFF as implemented in MacroModel (Halgren, T. A. J. Comput. Chem. 1996, 17, 490; 520; 553; 587; 616) and conformational searches were performed with the Monte Carlo routine (Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110). We thank Dr. P. O. Norrby for help and advice regarding the computational studies.
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