A short synthesis of (±)-methylenolactocin

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4809-4810

  Sarkar, Subrata ^a   Ghosh, Subrata ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; METHYLENOLACTOCIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030199656     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00942-2     Document Type: Article

References (10)

1. 1. Park, B. K.; Nakagawa, M ; Hirota, A., Nakayama, M. J. Antibiot. 1988, 41, 751.
2. 2. a) de Azevedo, M.B.M.; Murta, M.M.; Greene, A.E. J.Org.Chem. 1992, 57, 4567.
3. b) Honda, T .; Kimura ,N. J. Chem. Soc.,Chem. Commun .1994, 77.
4. c) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 23
5. d) Zhu, G.; Lu, X. J.Org.Chem. 1995, 60, 1087 .
6. e) Mawson, S.D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
7. 3. Maiti, G.; Roy, S.C. J. Chem. Soc.,Perkin Trans I 1996, 0000.
8. 4. The exclusive exo adduct 4 can be prepared from Diels-Alder reaction of itaconic anhydride with cyclopentadiene followed by hydrolysis and esterification ( Fotiadu, F. ; Michel, F.; Buono, G. Tetrahedron Lett. 1990, 31, 4863.).
9. 4 ) 0.91(br s, 3H),1.38(br, 10H), 1.83-2.30(m, 2H) ,2.58 and 2.73 (both d, J = 3Hz, 1H), 2.93 (br s, 2H), 3.63 and 3.76 (both s, 3H), 4.0-4.63(m, 1H) and 5.83 - 6.53(m, 2H).7 , δ(200MHz) 0.88(t, J = 6 Hz, 6H), 1.29(m, 6H), 1.58(m,2H), 3.75 (s, 3H), 4.59 (m,1H), 5.81 (d, J = 2Hz ,1H) and 6.40(d ,J = 2Hz, 1H). 1,δ (200 MHz ) 0.89(brs, 3H), 1.20-1.75 (m, 8H),3.60(m, 1H), 4.80(q, J = 6.4Hz), 6.00 ( d, J = 2.6Hz) and 6.44 (d, J = 2.6Hz, 1H).
10. 1H NMR reported (ref. 3 ) by Roy et al of this laboratory.