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Volumn 66, Issue 7, 2001, Pages 2350-2357

A novel route to the marasmane skeleton via a tandem rearrangement-cyclopropanation reaction. Total synthesis of (+)-isovelleral

(3) Bell, R P L a Wijnberg, J B P A a De Groot, A a

a WAGENINGEN UNIVERSITY (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANATION REACTION;

CATALYSIS; ETHERS; MAGNESIUM COMPOUNDS;

SYNTHESIS (CHEMICAL);

1A,2,5,5,6B PENTAMETHYL 1,1A,3A,4,5,6,6A,6B OCTAHYDROCYCLOPROPA[E]INDENE; 1A,2,5,5,6B PENTAMETHYLDECAHYDROCYCLOPROPA[E]INDEN 2 OL; ETHER DERIVATIVE; ISOVELLERAL; MARASMANE; NAPHTHALENE DERIVATIVE; NAPHTHALENONE; SESQUITERPENE DERIVATIVE; TRIMETHYLSILYL ENOL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

BASIDIOMYCOTA; CYCLOPROPANES; INDENES; MESYLATES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SESQUITERPENES;

EID: 0035815140 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0015568 Document Type: Article

Times cited : (29)

References (58)

1
- 77957046829
- Atta-ur-Rahman, Ed.; Elsevier: Amsterdam
- (1995) Studies in Natural Product Chemistry , vol.17 , pp. 153-206
- Vidari, G.¹ Vita-Finzi, P.²

2
- 0002162017
- (1999) Progr. Chem. Org. Nat. Prod. , vol.77 , pp. 69
- Daniewski, W.M.¹ Vidari, G.²

3
- 0000606817
- (1983) J. Chem. Ecol. , vol.9 , pp. 1439
- Camazine, S.M.¹ Resch, J.F.² Eisner, T.³ Meinwald, J.⁴

4
- 0000343641
- (1985) J. Nat. Prod. , vol.48 , pp. 279
- Sterner, O.¹ Bergman, R.² Kihlberg, J.³ Wickberg, B.⁴

5
- 0001370273
- (1985) Tetrahedron Lett. , vol.26 , pp. 3163
- Sterner, O.¹ Bergman, R.² Franzen, C.³ Wickberg, B.⁴

6
- 0025874657
- (1991) Planta Medica , vol.57 , pp. 344
- Anke, H.¹ Sterner, O.²

7
- 0000082035
- (1993) Phytochemistry , vol.32 , pp. 1499
- Daniewski, W.M.¹ Gumulka, M.² Pankowska, E.³ Ptaszynska, K.⁴ Bloszyk, E.⁵ Jacobsson, U.⁶ Norin, T.⁷

8
- 0029158204
- (1995) Phytochemistry , vol.38 , pp. 1161
- Daniewski, W.M.¹ Gumulka, M.² Przesmycka, D.³ Ptaszynska, K.⁴ Bloszyk, E.⁵ Drozdz, B.⁶

9
- 0003503408
- note

10
- 0003651580
- Chapman & Hall: London
- (1991) Dictionary of Terpenoids , vol.1 , pp. 553-554
- Connolly, J.D.¹ Hill, R.A.²

11
- 0001305114
- (1977) J. Org. Chem. , vol.42 , pp. 2518
- Howard, B.M.¹ Fenical, W.²

12
- 0003585311
- See Scheme 1 and ref 7e

13
- 0025307852
- (1990) J. Org. Chem. , vol.55 , pp. 941
- Wijnberg, J.B.P.A.¹ Jenniskens, L.H.D.² Brunekreef, G.A.³ De Groot, A.⁴

14
- 0001599922
- (1991) J. Org. Chem. , vol.56 , pp. 6585
- Jenniskens, L.H.D.¹ Wijnberg, J.B.P.A.² De Groot, A.³

15
- 0028316329
- (1994) J. Org. Chem. , vol.59 , pp. 374
- Orru, R.V.A.¹ Wijnberg, J.B.P.A.² Bouwman, C.T.³ De Groot, A.⁴

16
- 0030036246
- (1996) Chem. Pharm. Bull. , vol.44 , pp. 1400
- Piet, D.P.¹ Orru, R.V.A.² Jenniskens, L.H.D.³ Van de Haar, C.⁴ Van Beek, T.A.⁵ Franssen, M.C.R.⁶ Wijnberg, J.B.P.A.⁷ De Groot, A.⁸

17
- 0002470977
- (1998) J. Org. Chem. , vol.63 , pp. 122
- Bell, R.P.L.¹ Sobolev, A.² Wijnberg, J.B.P.A.³ De Groot, A.⁴

18
- 0030061066
- (1996) Bull. Chem. Soc. Jpn. , vol.69 , pp. 31
- Nagasawa, T.¹ Handa, Y.² Onoguchi, Y.³ Suzuki, K.⁴

19
- 0001566440
- (1986) Tetrahedron Lett. , vol.27 , pp. 2905
- Tobe, Y.¹ Sato, J.-I.² Sorori, T.³ Kakiuchi, K.⁴ Odaira, Y.⁵

20
- 0003665513
- The energy difference calculations were carried out with B3LYP/6-31G(d,p) using the GAUSSIAN 98 program (Revision A.7), Gaussian, Inc., Pittsburgh, PA
- (1998)

21
- 0003500143
- The experimental details are available as Supporting Information

22
- 33845556313
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 5454
- Gemal, A.L.¹ Luche, J.-L.²

23
- 0003588592
- note

24
- 0002667764
- (1981) Synthesis , pp. 1
- Mitsunobu, O.¹

25
- 0003508114
- 3AlH was also employed successfully in the key step of the total synthesis of furanether B. See ref 7e

26
- 0003504685
- note

27
- 0000591281
- (1969) Tetrahedron Lett. , pp. 2145
- Ireland, R.E.¹ Pfister, G.²

28
- 0003583107
- note

29
- 84982067015
- (1980) Chem. Ber. , vol.113 , pp. 1907
- Gerdes, H.¹ Javeri, S.² Marschall, H.³

30
- 0000978425
- (1983) Bull. Chem. Soc. Jpn. , vol.56 , pp. 1095
- Kawana, M.¹ Koresawa, T.² Kuzuhara, H.³

31
- 0003592377
- note

32
- 0002452640
- (1976) Bull. Soc. Chim. Fr. , pp. 169
- Place, P.¹ Roumestant, M.-L.² Gore, J.³

33
- 0000846427
- (1993) J. Org. Chem. , vol.58 , pp. 1199
- Orru, R.V.A.¹ Wijnberg, J.B.P.A.² Jenniskens, L.H.D.³ De Groot, A.⁴

34
- 0001625286
- (1969) J. Org. Chem. , vol.34 , pp. 3587
- Dauben, W.G.¹ Lorber, M.² Fullerton, D.S.³

35
- 84989484020
- (1979) Synthesis , pp. 730
- Miller, R.D.¹ McKean, D.R.²

36
- 0003658391
- note

37
- 0003507162
- note

38
- 0003500147
- note

39
- 0003659543
- note

40
- 0000682539
- (1980) Tetrahedron Lett. , vol.21 , pp. 4313
- McMurry, J.E.¹ Scott, W.J.²

41
- 0026700793
- (1992) J. Org. Chem. , vol.57 , pp. 3822
- Hansson, T.¹ Sterner, O.² Wickberg, B.³

42
- 0026472609
- (1992) J. Org. Chem. , vol.57 , pp. 5979
- Thompson, S.K.¹ Heathcock, C.H.²

43
- 0003581549
- (1990) J. Chem. Soc., Chem. Commun. , vol.865
- Bergman, R.¹ Hansson, T.² Sterner, O.³ Wickberg, B.⁴

44
- 0003501404
- note

45
- 0030013187
- (1996) Synth. Commun. , vol.26 , pp. 945
- Hanselmann, R.¹ Benn, M.²

46
- 0033575372
- (1999) Tetrahedron: Asymm. , vol.10 , pp. 2729
- Franssen, M.C.R.¹ Jongejan, H.² Kooijman, H.³ Spek, A.L.⁴ Bell, R.P.L.⁵ Wijnberg, J.B.P.A.⁶ De Groot, A.⁷

47
- 0003661698
- note

48
- 0024999836
- (1990) Chem. Pharm. Bull. , vol.38 , pp. 2435
- Nakamura, H.¹ Arata, K.² Wakamatsu, T.³ Ban, Y.⁴ Shibasaki, M.⁵

49
- 0003706029
- note

50
- 0003584860
- note

51
- 0003581551
- In contrast to 43, enol triflate formation proceeded smoothly with the compound possessing an ester group instead of an aldehyde function at C8. See ref 31

52
- 0003659545
- note

53
- 0003586110
- The use of PCC resulted in a modest yield (25%) of 48. Swern oxidation of 47 may give a better result. See ref 31

54
- 0000379261
- (1996) J. Org. Chem. , vol.61 , pp. 3820
- Wu, H.-J.¹ Lin, C.-C.²

55
- 0031575616
- (1997) Tetrahedron , vol.53 , pp. 2401
- Wu, H.-J.¹ Chern, J.-H.² Wu, C.-Y.³

56
- 0003556339
- (1986) Can. J. Chem. , vol.64 , pp. 1553
- Griesbaum, K.¹ Bandyopadhyay, A.R.² Meister, M.³

57
- 0003493305
- note

58
- 0003505899
- note

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