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Tetrahedron Letters

Volumn 19, Issue 26, 1978, Pages 2301-2304

Cyclization of ω-trimethylsilylethynylalkanoyl chlorides. Application of the preparation of large ring ynones and dl- and (R)-muscone

(4) Utimoto, Kiitiro a Tanaka, Michio a Kitai, Mitsumasa a Nozaki, Hitosi a

a KYOTO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001856918 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)91520-5 Document Type: Article

Times cited : (59)

References (46)

1
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- (1975) J. Am. Chem. Soc. , vol.97 , pp. 1264
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2
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- Karpf¹ Dreiding²

3
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- Karpf¹ Dreiding²

4
- 0017104072
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- Fischli¹ Branca² Daly³

5
- 84963184494
- Eine chiral �konomische Totalsynthese von (R)- und (S)-Muskon via Epoxysulfoncyclofragmentierung
- (1977) Helvetica Chimica Acta , vol.60 , pp. 925
- Branca¹ Fischli²

6
- 34250757893
- (1976) Tetrahedron Lett. , pp. 3585
- Baumann¹ Hoffmann² Müller³

7
- 0001191633
- A Facile Ring Enlargement Reaction via β-Oxido Carbenoid
- (1977) Bulletin of the Chemical Society of Japan , vol.50 , pp. 1592
- Taguchi¹ Yamamoto² Nozaki³

8
- 0017412715
- (1977) J. Org. Chem. , vol.42 , pp. 2326
- Ito¹ Saegusa²

9
- 0000417977
- (1964) Tetrahedron , vol.20 , pp. 2601
- Mamdapur¹ Pai² Chakravarti³ Nayak⁴ Bhattacharyya⁵

10
- 0000700240
- (1951) Arkiv Kemi , vol.3 , pp. 517
- Ställberg-Stenhagen¹

11
- 84914408284
- SYNTHESIS OF dl-MUSCONE
- (1977) Chemistry Letters , pp. 715
- Nokami¹ Kusumoto² Jinnai³ Kawada⁴

12
- 7644240506
- Substitutions- und Additionsreaktionen an silylierten Acetylenen
- Intermolecular acylation of trimethylsilylacetylenes has been published
- (1963) Chemische Berichte , vol.96 , pp. 3280
- Birkofer¹ Ritter² Uhlenbrauck³

13
- 0015850630
- (1973) J. Org. Chem. , vol.38 , pp. 2254
- Newman¹

14
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- Walton¹ Wauch²

15
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- (1973) J. Organomet. Chem. , vol.59 , pp. C4
- Bourgeois¹ Merault² Calas³

16
- 84918951415
- High dilution apparatus of Davis was used
- (1977) Chem. Ind. (London) , pp. 203
- Davis¹

17
- 84918985792
- +, 2), 205 (2), 191 (4), 95 (49), 80 (71), 55 (71), 41 (100).

18
- 84918985790
- +, 3), 177 (2), 107 (42), 95 (41), 93 (46), 79 (100).

19
- 84918985788
- +, 7), 149 (9), 107 (51), 79 (100).

20
- 0000345883
- Formation of a mixture of the α,β-unsaturated ketone and its β,γ-isomer of 14-membered ring has been reported
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 1264
- Stork¹ Macdonald²

21
- 84918985786
- Structure was determined by the comparison of ir nmr, and ms with those of reported.

22
- 84918985783
- Prepared from (R)-citronellol (64% e.e.).

23
- 84918985780
- 4) δ ppm, 0.94 (3H, d, J = 7 Hz), 1.2–1.9 (19H, m), 2.2–2.4 (4H, m).

24
- 84963184494
- Eine chiral �konomische Totalsynthese von (R)- und (S)-Muskon via Epoxysulfoncyclofragmentierung
- 3-shifted nmr in which two doublets (C-methyl of R and S isomer, respectively) were observed. Synthesis of optically active muscone has appeared
- (1977) Helvetica Chimica Acta , vol.60 , pp. 925
- Branca¹ Fischli²

25
- 0000417977
- (1964) Tetrahedron , vol.20 , pp. 2601
- Mamdapur¹ Pai² Chakravarti³ Nayak⁴ Bhattacharyya⁵

26
- 0000700240
- (1951) Arkiv Kemi , vol.3 , pp. 517
- Ställberg-Stenhagen¹

27
- 84918985767
- (R)-Citronellol was used as “Chiral Pool” in this synthesis.

28
- 84918985766
- Formation of 3-chloro-2-trimethylsilyl-2-alkenones has not been described yet to the best of authors' knowledge.

29
- 84918985765
- +, 2), 175 (35), 173 (85), 93 (100).

30
- 84918985764
- 3-shifted nmr showed singlet (9H), triplet (2H), triplet (2H), and quintet (2H); ms m/e (rel. %), 187 (M-15, 90), 95 (42), 93 (100), 55 (40).

31
- 84918985762
- 3-shifted nmr supported the structure.

32
- 84918985760
- 4) δ ppm, 0.18 (9H, m), 1.5–1.9 (6H, m), 2.1–2.4 (2H, m), 2.4–2.7 (2H, m).

33
- 84918985758
- Prepared from propargyl alcohol and 1-bromododecane in 83% yield.

34
- 84918985757
- 4) δ ppm, 1.2–1.5 (23H, m), 1.75 (1H, J = 3 Hz), 2.0–2.3 (2H, m), 3.55 (2H, t, J = 7 Hz).

35
- 33847800586
- Isomerization of internal acetylenes to the corresponding terminal ones as well as its application to acetylenic alcohols
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 891
- Brown¹ Yamashita²

36
- 0011991624
- Exceptionally easy isomerization of acetylenic alcohols with potassium 3-aminopropylamide. A new, high yield synthesis of functionally differentiated ??-difunctional structures
- (1976) Journal of the Chemical Society, Chemical Communications , pp. 959
- Brown¹ Yamashita²

37
- 37049098951
- Novel synthesis of an ?-alkynylorganometallic reagent via triple bond isomerization with potassium 3-aminopropylamide: ?-(9-borabicyclo[3.3.1]nonan-9-yl)alkl-1-ynes
- (1977) Journal of the Chemical Society, Chemical Communications , pp. 318
- Brown¹ Negishi²

38
- 0002013029
- (1976) Tetrahedron Lett. , pp. 2565
- Lindhoudt¹ van Mourik² Pabon³

39
- 84983933784
- A modified procedure for the isomerization of alkynes and acetylenic alcohols to terminal acetylenes: (Preliminary communication)
- (1977) Recueil des Travaux Chimiques des Pays-Bas , vol.96 , pp. 160
- Hommes¹ Brandsma²

40
- 84918985755
- Sapporo, 1K11.
- (1976) 33rd Annual Meeting of Chemical Society of Japan
- Utimoto¹ Kitai² Nozaki³

41
- 84918985752
- 3SiCl then with water gave XII.

42
- 84918985739
- Chromic acid oxidation (Jones reagent) at 0°C.

43
- 84918985738
- −1.

44
- 33947089018
- 4 reduction:
- (1972) J. Org. Chem. , vol.37 , pp. 1542
- Noyori¹ Umeda² Ishigami³

45
- 84918985737
- Deuterium content was determined by ms of the corresponding trimethylsilyl ether.

46
- 84918985736
- The authors wish to thank the Ministry of Education, Japan, for Grant-in-Aid (110309, 203014 and partially 185188) .

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.