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Volumn 48, Issue 48, 2007, Pages 8442-8448

Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

Author keywords

Hiyama coupling; Macrolide antibiotics; Ring closing olefin metathesis; Transannular Diels Alder reaction; Tubelactomicins

Indexed keywords

MACROLIDE; TUBELACTOMICIN A; TUBELACTOMICIN E; UNCLASSIFIED DRUG;

EID: 35548977936     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.002     Document Type: Article
Times cited : (15)

References (22)
  • 3
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    • Takeuchi, T.; Igarashi, M.; Naganawa, H.; Hamada, M. Japan Patent JP2001-55386A, 2001.
  • 8
    • 4544332948 scopus 로고    scopus 로고
    • We have accomplished the total synthesis of macquarimicins using a TADA approach, see
    • 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
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11254-11267
    • Munakata, R.1    Katakai, H.2    Ueki, T.3    Kurosaka, J.4    Takao, K.5    Tadano, K.6
  • 9
    • 0000212392 scopus 로고
    • 2O workup (partial decomposition of 15 and 44% recovery of 15). For Lipshutz reagent in condition (1), see
    • 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
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2065-2068
    • Lipshutz, B.H.1    Ellsworth, E.L.2    Dimock, S.H.3    Reuter, D.C.4
  • 10
    • 0000390817 scopus 로고    scopus 로고
    • For a review on the Hiyama cross-coupling, see. Diederich F., and Stang P.J. (Eds), Wiley-VCH, Weinheim, Germany
    • 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
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 421-453
    • Hiyama, T.1
  • 16
    • 35549008577 scopus 로고    scopus 로고
    • note
    • 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.
  • 17
    • 1442360753 scopus 로고    scopus 로고
    • For reviews on olefin metathesis, see. Grubbs R.H. (Ed), Wiley-VCH, Weinheim
    • For reviews on olefin metathesis, see. In: Grubbs R.H. (Ed). Handbook of Metathesis (2003), Wiley-VCH, Weinheim
    • (2003) Handbook of Metathesis
  • 21
    • 10044263386 scopus 로고    scopus 로고
    • For our synthetic achievement of the mycoepoxydiene total synthesis using sequential ROM/cross/RCM reaction, see
    • 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
    • (2004) J. Org. Chem. , vol.69 , pp. 8789-8795
    • Takao, K.1    Yasui, H.2    Yamamoto, S.3    Sasaki, D.4    Kawasaki, S.5    Watanabe, G.6    Tadano, K.7
  • 22
    • 35548945928 scopus 로고    scopus 로고
    • note
    • To maintain the reproducibility of the TADA reaction, it is important to add the Grubbs catalyst (each 20 mol %) for two times.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.