Stereocontrolled synthesis of spirocyclopropane sugars and their application to asymmetric formation of tertiary chiral centres: A route to 2,2'-dialkylated pyranose subunit (C18-C23) of lasonolide A

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8617-8620

  Gurjar, Mukund K ^b   Kumar, Punit ^a   Venkateswara Rao, B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 16144365082     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01991-0     Document Type: Article

References (15)

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2. 2. Drug Data Report, 1996, 18, 90.
3. 3. Koto, S.; Takabe, Y. and Zen, S. Bull. Chem. Soc. Jpn., 1972, 45, 291-3.
4. 4. a) Furukawa, J.; Kawabata, N and Nishimura, J. Tetrahedron Lett., 1966, 3353-54.
5. b) Furukawa, J.; Kawabata, N and Nishimura, J. Tetrahedron , 1968, 24, 53-58.
6. c) Furukawa, J.; Kawabata, N and Nishimura, J. Tetrahedron Lett., 1968, 3495-98.
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8. e) Friedrich, E.C. and Biresaw, G. J. Org. Chem. 1982, 47, 1615-18.
9. 5. Wong, H.N.C.; Hon, Moon-Yuen.; Tse, Chun-wah and Yip, Yu-chi. Chem. Rev., 1989, 89, 165-198.
10. 6. Enders, D.; Noyori, R and Trost, B.M. Protecting Groups ; Thieme: Stuttgart, 1994, pp.46.
11. 7. Alternatively we attempted one carbon degradation of 9 by converting it into the ketone derivative (9a) by succesive Grignard reaction and PDC oxidation. The Baeyer-villiger oxidation of 9a only provided the 3-O-benzoate 9b. (formula presented)
12. 8. Freeman, P.K. and Swenson, K.E. J. Org. Chem., 1982, 47, 2033-39.
13. 9. Tsuchiya, T., Ajito, K., Umezawa, S and Ikeda, A. Carbohydrate Research., 1984, 126, 45-60.
14. 3) compound 19 : δ 0.06 (s, 6 H), 0.9 (s, 9H), 1.14 (s, 3 H), 1.5 -2.0 (m, 2 H), 2.06, 2.10 (2s, 6 H), 3.36 (s, 3 H), 3.64 (m, 2 H), 3.80, 4.30 (2d, 2 H, J= 12 Hz), 3.95 (m, 1 H), 4.36 (s, 1 H), 4.96 (bs, 1 H).
15. 1H-NMR, MS, HRMS and/or elemental analysis.