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Tetrahedron Letters

Volumn 21, Issue 33, 1980, Pages 3119-3122

Stereoselective total syntheses of (±)-warburganal and (±)-isotadeonal

(2) Kende, Andrew S a Blacklock, Thomas J a

a UNIVERSITY OF ROCHESTER (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; ISOTADEONAL; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION; THEORETICAL STUDY; WARBURGANAL;

EID: 0019219575 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)77424-7 Document Type: Article

Times cited : (44)

References (13)

1
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- Potent army worm antifeedants from the east African Warburgia plants
- (1976) Journal of the Chemical Society, Chemical Communications , pp. 1013-1014
- Kubo¹ Lee² Pettei³ Pilkiewicz⁴ Nakanishi⁵

2
- 84914251340
- SYNTHESES OF (±)-WARBURGANAL AND (±)-ISOTADEONAL
- (1979) Chemistry Letters , pp. 635-636
- Ohsuka¹ Matsukawa²

3
- 0001014844
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 4398-4400
- Tanis¹ Nakanishi²

4
- 33845560979
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 4400-4401
- Nakata¹ Akita² Naioto³ Oishi⁴

5
- 0000715935
- The Structure of Tadeonal and Isotadeonal, Components of Polygonum Hydropiper L
- (1963) Nippon kagaku zassi , vol.84 , pp. 748
- Ohsuka¹

6
- 0010402290
- Decalone 4 is available from 2-methyl-1,3-cyclohexanedione in 50% yield by the method of
- (1979) J. Org. Chem. , vol.44 , pp. 2838-2842
- Snitman¹ Tsai² Watt³ Edwards⁴ Stotter⁵

7
- 3042877635
- A Synthesis of 2-Formyl-5,5,9-trimethyl-trans-Δ2-1-octalone
- (1967) Bulletin of the Chemical Society of Japan , vol.40 , pp. 1730-1732
- Otatani¹ Kato² Kitahara³

8
- 84918079311
- While ylides such as those listed failed to react with ketoacetal 7 satisfactorily, it was found that 7 did readily undergo 1,2-addition with vinyl lithium, methyl lithium, and methyl magnesium bromide to afford high yields of the corresponding alcohols resulting exclusively from back side attack of the nucleophile.

9
- 37049106665
- Silicon in synthesis. Methoxymethyltrimethylsilane, a new reagent for reductive nucleophilic acylation
- (1979) Journal of the Chemical Society, Chemical Communications , pp. 822-823
- Magnus¹ Roy²

10
- 84918079310
- All new compounds gave satisfactory spectral and elemental analyses. Full experimental details will be presented in our forthcoming publication.

11
- 84918079309
- Stereochemical assignments of the enol ether adducts 9a and 9b and aldehydes 10a and 10b are provisional and based on the observation that the enol ether proton of aldehyde 10b (δ7.32) shows a 1.4 ppm downfield shift relative to the enol ether proton of 10a (δ5.92). Molecular models suggest that the enol ether proton of aldehyde 10b lies in the deshielding zone of the aldehyde carbonyl. This deshielding can only be present in adduct 10b. To further substantiate these stereochemical assignments, adduct 9b is currently undergoing single crystal X-ray structure determination.

12
- 85022697312
- Epoxyethers. IV. Mechanism of the Opening of an Epoxyether with an Organic Acid1
- For a discussion on the mechanism of a ring opening of an epoxy ether, see
- (1953) Journal of the American Chemical Society , vol.75 , pp. 5975-5978
- Stevens¹ Dykstra²

13
- 84918079308
- +, 3), 249 (2), 222 (19), 221 (base), 133 (29), 109 (76), 105 (38) and 95 (24).

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