1 Naturally occurring taxoids

作者: Giovanni Appendino

DOI: 10.1016/S0165-7208(06)80015-2

关键词:

摘要: Publisher Summary This chapter discusses naturally occurring taxoids. Taxoids are a structurally homogeneous class of compounds that occur in two genera the yew family (Taxus and Austrotaxus). Ancient trees like gingko storehouse biologically active compounds. having tricyclopentadecane ring system or closely related skeleta. Two planar representations taxane use—namely, (1) linear, (2) angular. Taxanes considered most widespread skeletal types In taxanes, site main structural variation terpenoid core is C-4/C-20/C-5 moiety. The tertiary hydroxyl at C-4 generally esterified, but secondary group C-5 primary one C-20 can both free esterified form. Oxo bridges always β, an important observation regard to biogenesis these types. All natural with exception taxagifine its derivatives have double bond C-11/C-12. plays role stabilizing twist-boat conformation cyclooctane moiety taxanes preventing transannular interaction between substituents C-3α C-12α.

参考文章(99)
Gerd Krüssmann, Handbuch der Nadelgehölze Paul Parey. ,(1972)
Bo LI, Kiyoshi TANAKA, Kaoru FUJI, Handong SUN, Tooru TAGA, None, THREE NEW DITERPENOIDS FROM TAXUS CHINENSIS Chemical & Pharmaceutical Bulletin. ,vol. 41, pp. 1672- 1673 ,(1993) , 10.1248/CPB.41.1672
Thomas V. Magee, William G. Bornmann, Richard C. A. Isaacs, Samuel J. Danishefsky, A straightforward route to functionalized intermediates containing the CD substructure of taxol. Journal of Organic Chemistry. ,vol. 57, pp. 3274- 3276 ,(1992) , 10.1021/JO00038A008
Michael J. Begley, Christopher B. Jackson, Gerald Pattenden, Investigation of transannular cyclisations of verticillanes to the taxane ring system Tetrahedron Letters. ,vol. 26, pp. 3397- 3400 ,(1985) , 10.1016/S0040-4039(00)98307-2
K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, R. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladouros, K. Paulvannan, E. J. Sorensen, Total synthesis of taxol Nature. ,vol. 367, pp. 630- 634 ,(1994) , 10.1038/367630A0
Giovanni Appendino, Luciano Barboni, Pierluigi Gariboldi, Ezio Bombardelli, Bruno Gabetta, Davide Viterbo, Revised structure of brevifoliol and some baccatin VI derivatives Journal of the Chemical Society, Chemical Communications. pp. 1587- 1589 ,(1993) , 10.1039/C39930001587
D. P. Della Casa de Marcano, T. G. Halsall, G. M. Hornby, The structure of baccatin-III, a partially esterified octahydroxy-monoketo-taxane derivative lacking a double bond at C-4 Journal of the Chemical Society D: Chemical Communications. pp. 216b- ,(1970) , 10.1039/C2970000216B
Lolita O. Zamir, Maria E. Nedea, François X. Garneau, Biosynthetic building blocks of taxanes Tetrahedron Letters. ,vol. 33, pp. 5235- 5236 ,(1992) , 10.1016/S0040-4039(00)79141-6
Robert A Holton, Hyeong Baik Kim, Carmen Somoza, Feng Liang, Ronald J Biediger, P Douglas Boatman, Mitsuru Shindo, Chase C Smith, Soekchan Kim, None, First total synthesis of taxol. 2. Completion of the C and D rings Journal of the American Chemical Society. ,vol. 116, pp. 1599- 1600 ,(1994) , 10.1021/JA00083A067
Wenwen Ma, Gary L. Park, George A. Gomez, Matthew H. Nieder, Tom L. Adams, John S. Aynsley, Om P. Sahai, Richard J. Smith, Roy W. Stahlhut, Peter J. Hylands, Francis Bitsch, Cedric Shackleton, New bioactive taxoids from cell cultures of Taxus baccata. Journal of Natural Products. ,vol. 57, pp. 116- 122 ,(1994) , 10.1021/NP50103A016