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Volumn 44, Issue 4, 1996, Pages 715-719

A formal asymmetric synthesis of Calabar bean alkaloids

Author keywords

( ) eserethole; ( )physostigmine; aromatization; asymmetric nitroolefination; Diels Alder reaction; nitro group

Indexed keywords

2 METHYL 2 (2 NITROETHENYL) DELTA VALEROLACTONE; ALKALOID; CHOLINESTERASE INHIBITOR; ESERETHOLE; ESERIDINE; LACTONE; NITRO DERIVATIVE; PHYSOSTIGMINE; PHYSOSTIGMINE DERIVATIVE; PHYSOVENINE; UNCLASSIFIED DRUG;

EID: 0029919045     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.715     Document Type: Article
Times cited : (43)

References (70)
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    • ed. by Brossi A., Academic Press, New York
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    • The exo selective Diels Alder reaction of nitroolefins with Danishefsky's diene was generalized and will be reported elsewhere. See the following references on the endo selective Diels-Alder reaction of nitroolefins with Danishefsky's diene: a) Ono N., Miyake H., Kamimura A., Kaji A., J. Chem. Soc., Perkin Trans. 1, 1987, 1929-1935;
    • J. Chem. Soc., Perkin Trans. 1 , vol.1987 , pp. 1929-1935
    • Ono, N.1    Miyake, H.2    Kamimura, A.3    Kaji, A.4
  • 48
    • 0007906819 scopus 로고    scopus 로고
    • We found a new type of aromatization of the six-membered ring of 5 under acidic conditions (p-TsOH, MeOH) to the anisole derivative, and applied it to the asymmetric syntheses of (-)-aphanorphine and (-)-eptazocine, see: Node M., Imazato H., Kurosaki R., Kawano Y., Inoue T., Nishide K., Fuji K., Heterocycles, 42, 811-819 (1996).
    • (1996) Heterocycles , vol.42 , pp. 811-819
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  • 49
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    • note
    • The reduction of the nitro group in 5 under usual conditions with palladium carbon in a hydrogen atmosphere did not occur.
  • 54
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    • (-)-Eserethole, see 7a, 19a. dl-Eserethole, see 7b, and Smith R., Livinghouse T., J. Org. Chem., 48, 1554-1555 (1983).
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    • Physovenine: structure; a) Robinson B., J. Chem. Soc., 1964, 1503-1506.
    • J. Chem. Soc. , vol.1964 , pp. 1503-1506
    • Robinson, B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.