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Igarashi, M.1
Hayashi, C.2
Homma, Y.3
Hattori, S.4
Kinoshita, N.5
Hamada, M.6
Takeuchi, T.7
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3
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35548944162
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Takeuchi, T.; Igarashi, M.; Naganawa, H.; Hamada, M. Japan Patent JP2001-55386A, 2001.
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4
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20444505606
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Motozaki T., Sawamura K., Suzuki A., Yoshida K., Ueki T., Ohara A., Munakata R., Takao K., and Tadano K. Org. Lett. 7 (2005) 2261-2264
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(2005)
Org. Lett.
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Motozaki, T.1
Sawamura, K.2
Suzuki, A.3
Yoshida, K.4
Ueki, T.5
Ohara, A.6
Munakata, R.7
Takao, K.8
Tadano, K.9
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5
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20444431520
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Motozaki T., Sawamura K., Suzuki A., Yoshida K., Ueki T., Ohara A., Munakata R., Takao K., and Tadano K. Org. Lett. 7 (2005) 2265-2267
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(2005)
Org. Lett.
, vol.7
, pp. 2265-2267
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Motozaki, T.1
Sawamura, K.2
Suzuki, A.3
Yoshida, K.4
Ueki, T.5
Ohara, A.6
Munakata, R.7
Takao, K.8
Tadano, K.9
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7
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34547619044
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Sawamura K., Yoshida K., Suzuki A., Motozaki T., Kozawa I., Hayamizu T., Munakata R., Takao K., and Tadano K. J. Org. Chem. 72 (2007) 6143-6148
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(2007)
J. Org. Chem.
, vol.72
, pp. 6143-6148
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Sawamura, K.1
Yoshida, K.2
Suzuki, A.3
Motozaki, T.4
Kozawa, I.5
Hayamizu, T.6
Munakata, R.7
Takao, K.8
Tadano, K.9
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8
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4544332948
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We have accomplished the total synthesis of macquarimicins using a TADA approach, see
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We have accomplished the total synthesis of macquarimicins using a TADA approach, see. Munakata R., Katakai H., Ueki T., Kurosaka J., Takao K., and Tadano K. J. Am. Chem. Soc. 126 (2004) 11254-11267
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11254-11267
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Munakata, R.1
Katakai, H.2
Ueki, T.3
Kurosaka, J.4
Takao, K.5
Tadano, K.6
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9
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0000212392
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2O workup (partial decomposition of 15 and 44% recovery of 15). For Lipshutz reagent in condition (1), see
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2O workup (partial decomposition of 15 and 44% recovery of 15). For Lipshutz reagent in condition (1), see. Lipshutz B.H., Ellsworth E.L., Dimock S.H., and Reuter D.C. Tetrahedron Lett. 30 (1989) 2065-2068
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(1989)
Tetrahedron Lett.
, vol.30
, pp. 2065-2068
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Lipshutz, B.H.1
Ellsworth, E.L.2
Dimock, S.H.3
Reuter, D.C.4
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10
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0000390817
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For a review on the Hiyama cross-coupling, see. Diederich F., and Stang P.J. (Eds), Wiley-VCH, Weinheim, Germany
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For a review on the Hiyama cross-coupling, see. Hiyama T. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim, Germany 421-453
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(1998)
Metal-Catalyzed Cross-Coupling Reactions
, pp. 421-453
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Hiyama, T.1
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16
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35549008577
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note
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Regarding the low endo/exo-selectivities observed in the TADA reactions of 15, 6, and 31 (in Scheme 6), we do not have reasonable explanation. On the other hand, we previously found the following experimental result during studies on the IMDA reactions for the stereoselective construction of the octahydronaphthalene part. Thus, when the bulkiness of the dienophile part increased, the endo/exo-selectivity of the IMDA reaction reduced remarkably. In the case of the substrate possessing a CH{double bond, long}CHCOOR dienophile part in place of a CH{double bond, long}CHCHO functionality, the IMDA reaction provided a mixture of endo/exo-adducts in a 1:2 ratio. We speculate that this lack of the endo/exo-selectivity may arise from less effective secondary orbital interactions and/or increasing steric hindrances of the dienophile part in the transition-state of the IMDA reactions.
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17
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1442360753
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For reviews on olefin metathesis, see. Grubbs R.H. (Ed), Wiley-VCH, Weinheim
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For reviews on olefin metathesis, see. In: Grubbs R.H. (Ed). Handbook of Metathesis (2003), Wiley-VCH, Weinheim
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(2003)
Handbook of Metathesis
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19
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34447259779
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For a recent paper on the 12-membered macrolactone formation using RCM, see
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For a recent paper on the 12-membered macrolactone formation using RCM, see. Kanda R.M., Itoh D., Nagai M., Niijima J., Asai N., Mizui Y., Abe S., and Kotaka Y. Angew. Chem., Int. Ed. 46 (2007) 4350-4355
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(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 4350-4355
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Kanda, R.M.1
Itoh, D.2
Nagai, M.3
Niijima, J.4
Asai, N.5
Mizui, Y.6
Abe, S.7
Kotaka, Y.8
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21
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10044263386
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For our synthetic achievement of the mycoepoxydiene total synthesis using sequential ROM/cross/RCM reaction, see
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For our synthetic achievement of the mycoepoxydiene total synthesis using sequential ROM/cross/RCM reaction, see. Takao K., Yasui H., Yamamoto S., Sasaki D., Kawasaki S., Watanabe G., and Tadano K. J. Org. Chem. 69 (2004) 8789-8795
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(2004)
J. Org. Chem.
, vol.69
, pp. 8789-8795
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Takao, K.1
Yasui, H.2
Yamamoto, S.3
Sasaki, D.4
Kawasaki, S.5
Watanabe, G.6
Tadano, K.7
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22
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35548945928
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note
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To maintain the reproducibility of the TADA reaction, it is important to add the Grubbs catalyst (each 20 mol %) for two times.
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