메뉴 건너뛰기




Volumn 53, Issue 28, 1997, Pages 9585-9598

Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (-)- picropodophyllone

Author keywords

[No Author keywords available]

Indexed keywords

FARGESIN; HEMPA; LIGNAN DERIVATIVE; LITHIUM DERIVATIVE; PICROPODOPHYLLONE; UNCLASSIFIED DRUG;

EID: 0030837529     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00643-1     Document Type: Article
Times cited : (27)

References (48)
  • 2
    • 84889536594 scopus 로고
    • Cambridge University Press: New York
    • a) Lignans, Ayres, D. C.; Loike, J. D., Ed.; Cambridge University Press: New York, 1990.
    • (1990)
    • Lignans, A.D.C.1    Loike, J.D.2
  • 5
    • 0025080417 scopus 로고
    • Review on asymmetric synthesis of lignans: Ward, R. S. Tetrahedron 1990, 46, 5029.
    • (1990) Tetrahedron , vol.46 , pp. 5029
    • Ward, R.S.1
  • 29
    • 84889544137 scopus 로고    scopus 로고
    • note
    • 8c By using this method, 4 and 12 were converted into 13 and 14 quantitatively.
  • 30
    • 84889546779 scopus 로고    scopus 로고
    • note
    • Crystal data for 14 has been deposited at the Cambridge Crystallographic Data Centre.
  • 32
    • 0343825926 scopus 로고
    • Some stereoselective reactions on the basis of the stereocontrol induced by the 1,3-allylic strain have been reported: a) Tomioka, K; Kawasaki, H.; Yasuda, K.; Koga, K. Tetrahedron Lett. 1986, 27, 3247.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 3247
    • Tomioka, K.1    Kawasaki, H.2    Yasuda, K.3    Koga, K.4
  • 35
    • 0028270864 scopus 로고
    • The diastereoselective Michael addition reaction of nitromethyl anion and the lithium enolate to the ester 2 have been reported. In the case of nitromethyl anion, the selectivity was elucidated by the stereocontrol based on the 1,3-allylic strain. The present reaction is the first example of the diastereoselective Michael addition of an acyl anion equivalent to 2: a) Patrocinio, V. L.; Costa, P. R. R.; Correia, C. R. D. Synthesis 1994, 474.
    • (1994) Synthesis , pp. 474
    • Patrocinio, V.L.1    Costa, P.R.R.2    Correia, C.R.D.3
  • 37
    • 0009406158 scopus 로고
    • The stereochemical outcome could be elucidated by using either s-cis and s-trans conformation of 2 and 10. Houk and co-workers have reported that s-cis conformation is slightly preferred to s-trans one in the transition state of the Michael addition reaction of a lithium amide to methyl crotonate. According to their result, the transition structures in Fig. 1 and Fig. 2 were shown utilizing the s-cis conformation: a) Rudolf, K.; Hawkins, J. M.; Loncharich, R. J.; Houk, K. N. J. Org. Chem. 1988, 53, 3879.
    • (1988) J. Org. Chem. , vol.53 , pp. 3879
    • Rudolf, K.1    Hawkins, J.M.2    Loncharich, R.J.3    Houk, K.N.4
  • 39
    • 84889554050 scopus 로고    scopus 로고
    • note
    • The Michael addition of the corresponding dithiane compound to 2 was examined under the similar reaction conditions, however the diastereoselectivity was only 56% de. The rather smaller bulkiness of the 1,3-dithiane compound would brought about the low diastereoselectivity even in the presence of HMPA. (formula presented)
  • 40
    • 84889553150 scopus 로고    scopus 로고
    • note
    • 1H NMR. The mixture was subjected to the next reaction without separation because both isomers were convertible into (+)-fargesin. Crystal data for 16a has been deposited at the Cambridge Crystallographic Data Centre. (formula presented)
  • 41
    • 84889528309 scopus 로고    scopus 로고
    • note
    • 8h The optical purity of synthesized 6 was determined to be over 99% ee by HPLC. Theoretically, obtained 6 was 93% ee, but removal of the enantiomer would be achieved in the crystallization step of tetraol 20.
  • 42
    • 0026647113 scopus 로고
    • Review on synthesis of podophyllotoxin and related compounds: Ward, R. S. Synthesis 1992, 719.
    • (1992) Synthesis , pp. 719
    • Ward, R.S.1
  • 46
    • 84889558753 scopus 로고    scopus 로고
    • note
    • Oxidation of diol 22 was proceeded stereoselectively and no stereoisomer was obtained.
  • 47
    • 84889543624 scopus 로고    scopus 로고
    • note
    • In order to clarify whether racemization took place or not in the transformation of 21 to 23, 21 a and 21b were isolated and independently subjected to the transformation under the same reaction conditions. As a result, 21a and 21b were converted into 23a and 23b respectively without contamination of the isomer. (formula presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.