Taxane diterpenes 1. Control of relative and absolute stereochemistry in intramolecular pyrylium ylide-alkene cyclizations for the synthesis of taxol precursors

W.E. Bauta, J. Booth, M.E. Bos, M. DeLuca, L. Diorazio, T.J. Donohoe, C. Frost, N. Magnus, P. Magnus, J. Mendoza, P. Pye, J.G. Tarrant, S. Thom, F. Ujjainwalla

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Intramolecular pyrylium ylide-alkene cyclizations provide control of the absolute stereochemistry at the crucial C-19 angular methyl group, and leads to bicyclo[5.4.03,8]undecenones that contain the structural elements of the B/C rings of the taxanes.

LanguageEnglish
Pages14081-14102
Number of pages22
JournalTetrahedron
Volume52
Issue number45
DOIs
StatusPublished - 4 Nov 1996

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Taxoids
Stereochemistry
Diterpenes
Cyclization
Alkenes
Paclitaxel
taxane

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Taxane diterpenes 1. Control of relative and absolute stereochemistry in intramolecular pyrylium ylide-alkene cyclizations for the synthesis of taxol precursors. / Bauta, W.E.; Booth, J.; Bos, M.E.; DeLuca, M.; Diorazio, L.; Donohoe, T.J.; Frost, C.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.G.; Thom, S.; Ujjainwalla, F.

In: Tetrahedron, Vol. 52, No. 45, 04.11.1996, p. 14081-14102.

Research output: Contribution to journalArticle

Bauta, WE, Booth, J, Bos, ME, DeLuca, M, Diorazio, L, Donohoe, TJ, Frost, C, Magnus, N, Magnus, P, Mendoza, J, Pye, P, Tarrant, JG, Thom, S & Ujjainwalla, F 1996, 'Taxane diterpenes 1. Control of relative and absolute stereochemistry in intramolecular pyrylium ylide-alkene cyclizations for the synthesis of taxol precursors', Tetrahedron, vol. 52, no. 45, pp. 14081-14102. https://doi.org/10.1016/0040-4020(96)00867-8
Bauta, W.E. ; Booth, J. ; Bos, M.E. ; DeLuca, M. ; Diorazio, L. ; Donohoe, T.J. ; Frost, C. ; Magnus, N. ; Magnus, P. ; Mendoza, J. ; Pye, P. ; Tarrant, J.G. ; Thom, S. ; Ujjainwalla, F. / Taxane diterpenes 1. Control of relative and absolute stereochemistry in intramolecular pyrylium ylide-alkene cyclizations for the synthesis of taxol precursors. In: Tetrahedron. 1996 ; Vol. 52, No. 45. pp. 14081-14102.
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