Furanophane transannular Diels-Alder approach to (+)-chatancin: An asymmetric total synthesis of (+)-anhydrochatancin

Journal of Organic Chemistry

Volumn 68, Issue 18, 2003, Pages 6847-6852

  Toró, András ^a,b   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b ARRAY BIOPHARMA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; GENETIC ENGINEERING; HYDRIDES;

BIOGENETICS;

ORGANIC COMPOUNDS;

4A,7 DIMETHYL 1 OXO 2 ISOPROPYL 10 METHOXYCARBONYL 1,2,3,4,4A,4B,5,6,7,10A DECAHYDROPHENANTHRENE; ALDEHYDE; ANHYDROCHATANCIN; CHATANCIN; DILITHIOFUROIC ACID; DITERPENE; FURAN DERIVATIVE; FURANOCEMBRANOID; FURANOPHANE; METHYL 11 OXO 10 ISOPROPYL 3,7 DIMETHYL 15 OXABICYCLO[10.2.1]PENTADECA 1(14),6,12 TRIENE 13 CARBOXYLATE; METHYL 2 (1 OXO 2 ISOPROPYL 5 METHYLHEX 5 ENYL) 5 (2' METHYLHEX 5' ENYL)FURAN 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DIELS ALDER REACTION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

ALDEHYDES; ANTHOZOA; CYCLIZATION; DITERPENES; FURANS; INDICATORS AND REAGENTS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 0041837463     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034123o     Document Type: Article

References (46)

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23. For reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Fürstner, A. Top. Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-188. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Ivin, K. J. J. Mol. Catal. A.: Chem. 1998, 133, 1-16. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal A.: Chem. 1998, 133, 29-40. (i) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (j) Truka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (k) Hoveyda, A. H.; Schrock, R. H. Chem. Eur. J. 2001, 7, 945-950. (l) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
24. For reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Fürstner, A. Top. Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-188. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Ivin, K. J. J. Mol. Catal. A.: Chem. 1998, 133, 1-16. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal A.: Chem. 1998, 133, 29-40. (i) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (j) Truka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (k) Hoveyda, A. H.; Schrock, R. H. Chem. Eur. J. 2001, 7, 945-950. (l) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
25. For reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Fürstner, A. Top. Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-188. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Ivin, K. J. J. Mol. Catal. A.: Chem. 1998, 133, 1-16. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal A.: Chem. 1998, 133, 29-40. (i) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (j) Truka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (k) Hoveyda, A. H.; Schrock, R. H. Chem. Eur. J. 2001, 7, 945-950. (l) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
26. For reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Fürstner, A. Top. Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-188. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Ivin, K. J. J. Mol. Catal. A.: Chem. 1998, 133, 1-16. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal A.: Chem. 1998, 133, 29-40. (i) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (j) Truka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (k) Hoveyda, A. H.; Schrock, R. H. Chem. Eur. J. 2001, 7, 945-950. (l) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
27. For reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Fürstner, A. Top. Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-188. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Ivin, K. J. J. Mol. Catal. A.: Chem. 1998, 133, 1-16. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal A.: Chem. 1998, 133, 29-40. (i) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (j) Truka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (k) Hoveyda, A. H.; Schrock, R. H. Chem. Eur. J. 2001, 7, 945-950. (l) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
28. For reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Fürstner, A. Top. Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-188. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Ivin, K. J. J. Mol. Catal. A.: Chem. 1998, 133, 1-16. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal A.: Chem. 1998, 133, 29-40. (i) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (j) Truka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (k) Hoveyda, A. H.; Schrock, R. H. Chem. Eur. J. 2001, 7, 945-950. (l) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
29. For reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Fürstner, A. Top. Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-188. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (g) Ivin, K. J. J. Mol. Catal. A.: Chem. 1998, 133, 1-16. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal A.: Chem. 1998, 133, 29-40. (i) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (j) Truka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (k) Hoveyda, A. H.; Schrock, R. H. Chem. Eur. J. 2001, 7, 945-950. (l) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
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36. Obtained from (S)-(+)-piperitone, which is in turn derived from the commercially available (l)-menthone: (a) Dauben, W. G.; Thiessen, W. E.; Resnick, P. R. J. Org. Chem. 1965, 35, 1693-1698. (b) Hiroi, K.; Umemura, M. Tetrahedron 1993, 49, 1831-1840.
37. 1H NMR coupling constants and X-ray structural analysis data of our previously reported compounds (ref 6b) were used to identify the isomers.
38. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 1995, 34, 2039-2041.
39. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 953-956.
40. Purchased from Strem Chemicals, Inc., Newburyport, MA.
41. Schrock's catalyst 26 (Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. J. Am. Chem. Soc. 1990, 112, 3875-3886) gave the same compound.
42. This TTC triene, after desilylation, did not produce any TADA product due to the cis dienophile. It only underwent slow thermal decomposition in full accordance with our earlier observation (ref 6).
43. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
44. Fürstner, A.; Langemann, K. Synthesis 1997, 792-803.
45. 13C NM and IR spectra of 30 was identical to that of anhydrochatancin observed during the isolation and the previous total synthesis (ref 1).
46. 2 was not productive either.