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Tetrahedron Letters

Volumn 19, Issue 8, 1978, Pages 743-746

B-sulfinyl enones, synthons for terpenoid synthesis

(3) Bryson, T A a Dardis, R E a Gammill, R B a

a UNIVERSITY OF SOUTH CAROLINA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0141620105 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)85383-1 Document Type: Article

Times cited : (20)

References (24)

1
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2
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- Ireland¹ Marshall²

3
- 0005616156
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- Schultz¹ Kashdan²

4
- 0001513438
- and references therein
- (1971) JACS , vol.93 , pp. 1027
- Coates¹ Sowerby²

5
- 17444422782
- Vinylogous thioester chemistry: the total synthesis of desmethyl-β-cyperone
- (1975) Tetrahedron Letters , pp. 3793
- Gammill¹ Bryson²

6
- 84918269367
- (1976) Synthesis , vol.7 , pp. 416
- Gammill¹ Bryson²

7
- 0001373823
- For a review of Cu catalyzed alkyl lithium and alkyl Grignard reactions see, John Wiley and Sons
- (1975) Org. Reactions , vol.22 , pp. 253-400
- Posner¹

8
- 37049138008
- Reaction of lithium dialkylcuprates with ?-alkoxy and ?-alkylthio ??-unsaturated carbonyl compounds
- For addition of alkyl lithium to vinylogous thioesters see
- (1973) Journal of the Chemical Society, Chemical Communications , pp. 907
- Posner¹ Brunella²

9
- 0002721807
- THE STEREOSPECIFIC PREPARATION OF TRISUBSTITUTED OLEFINS
- also see
- (1973) Chemistry Letters , pp. 1097
- Kobayashi¹ Takei² Mukaritama³

10
- 0012757487
- For reaction of a dialkyl lithium cuprate with vinyl halides see
- (1970) J. Amer. Chem. Soc. , vol.92 , pp. 395
- Corey¹ Kuwajima²

11
- 84893434401
- University of South Carolina
- (1976) Ph.D. Thesis
- Gammill¹

12
- 1842501074
- Syntheses and Reactions of 2-Ethylthio- or 2-Phenylthio-2-cycloalkenones
- Sulfonium Salt Formation, see
- (1971) Bulletin of the Chemical Society of Japan , vol.44 , pp. 3155
- Mukaryama¹

13
- 0001126217
- The Chemistry of Trialkyloxonium Fluoroborates
- Meerwein's Salt, see
- (1971) Russian Chemical Reviews , vol.40 , Issue.9 , pp. 747
- Granik¹ Pyatur² Glushkov³

14
- 84918001875
- For magic methyl, see
- (1973) Chem. and Ind. , pp. 983
- Alder¹

15
- 4544298181
- (1962) J. Amer. Chem. Soc. , vol.84 , pp. 3701
- Leonard¹ Johnson²

16
- 0040365693
- Periodate Oxidation of Sulfides to Sulfoxides. Scope of the Reaction
- (1962) The Journal of Organic Chemistry , vol.27 , pp. 282
- Johnson¹ Sharp²

17
- 84918290121
- (1974) Syn. , pp. 47
- Heathcock¹ Clark²

18
- 84915492755
- (1970) Chem. and Ind. , pp. 1410
- Tamura¹

19
- 0000391618
- (1952) J. Amer. Chem. Soc. , vol.74 , pp. 831
- Fonken¹ Johnson²

20
- 84918290120
- Structures of vinylogous amides and esters previously prepared, see reference 5.

21
- 84948869172
- A New Synthesis and the13C-NMR OF β-Cyperone 1,3-Dibromo-2-Pentene, A New Ethyl Vinyl Ketone Equivalent
- (1976) Synthetic Communications , vol.6 , Issue.3 , pp. 5209
- Gammill¹ Bryson²

22
- 84918290119
- Dianion alkylation of compounds 7 and 10 were attempted with respect to formation of 25 and the analogous nitrile with only low yield conversions realized. Sulfur (α) alkylations and sulfoxide displacement was a vastly superior way of forming compounds like 25 from 1,3-cyclohexanedione.

23
- 84918290118
- All compounds exhibited satisfactory nmr, ir, uv, chromatography and mass spectral (or CH analysis) analytical data.

24
- 84918290117
- Other bases such as LDA and alkoxides were used; all showed low yields due to exchange, hydrolysis, decarboxylation, and/or formation of alkoxy enone.

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