A new method for the synthesis of medium- and large-sized carbocycles

Synlett

Volumn , Issue 5, 1999, Pages 647-649

  Masuya, Keiichi ^a   Tanino, Keiji ^b   Kuwajima, Isao ^c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c KITASATO INSTITUTE   (Japan)

Author keywords

Allylcation; Cyclization; Homoallylsilane; Lewis acid; Vinyl sulfide

Indexed keywords

CARBOCYCLE; TERPENOID; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032960729     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2696     Document Type: Article

References (17)

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4. For an example of an intramolecular cyclization reaction of allyl cation giving a large-sized carbocycle: Gassman, P. G.; Riehle, R. J. J. Am. Chem. Soc. 1989, 111, 2319.
5. For selected examples of intramolecular cyclization reactions of allyl cation: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1.
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9. (b) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 1724. Similar methylene-cyclopentane annulation could also be effected by using the substrate having a TMS-methyl group in place of the siloxy group. Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943.
10. (b) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 1724. Similar methylene-cyclopentane annulation could also be effected by using the substrate having a TMS-methyl group in place of the siloxy group. Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943.
11. It is reported that the C-C bond formation reaction between an enol silyl ether and a 1-(phenylthio)allyl cation occurs at the γ-position of sulfur: Hunter, R.; Simon, C. D. Tetrahedron Lett. 1986, 27, 1385.
12. These types of cyclization precursors were prepared in four steps from the corresponding alkyl iodide as shown below. The geometry of the double bond was determined by observation of NOE between the olefinic methyne proton and the methylthio group. (equation presented) For alkylation reactions of methylthiomethyl p-tolyl sulfone, see: Ogura, K.; Ohtsuki, K.; Nakamura, M.; Yahata, N.; Takahashi, K.; Iida, H. Tetrahedron Lett. 1985, 26, 2455.
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15. These types of cyclization precursors were prepared in three steps from the corresponding aldehyde as shown below: (equation presented)
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