92471-87-9Relevant academic research and scientific papers
Total synthesis of (+)-tedanolide
Smith III, Amos B.,Lee, Dongjoo
, p. 10957 - 10962 (2007)
A convergent, stereocontrolled total synthesis of (+)-tedanolide (1), an architecturally complex marine antitumor macrolide, has been achieved in 31 steps (longest linear sequence). Highlights of the synthesis comprise a highly efficient dithiane union, f
Total syntheses of (+)-tedanolide and (+)-13-deoxytedanolide
Dunetz, Joshua R.,Julian, Lisa D.,Newcom, Jason S.,Roush, William R.
supporting information; experimental part, p. 16407 - 16416 (2009/05/08)
Convergent total syntheses of the potent cytotoxins (+)-tedanolide (1) and (+)-13-deoxytedanolide (2) are described. The carbon framework of these compounds was assembled via a stereoselective aldol reaction that unifies the C(1)-C(12) ketone fragment 5 with a C(13)-C(23) aldehyde fragment 6 (for 13-deoxytedanolide) or 52 (for tedanolide). Multiple obstacles were encountered en route to (+)-1 and (+)-2 that required very careful selection and orchestration of the stereochemistry and functionality of key intermediates. Chief among these issues was the remarkable stability and lack of reactivity of hemiketals 33b and 34 that prevented the tedanolide synthesis from being completed from aldol 4. Key to the successful completion of the tedanolide synthesis was the observation that the 13-deoxy hemiketal 36 could be oxidized to C(11, 15)-diketone 38 en route to 13-deoxytedanolide. This led to the decision to pursue the tedanolide synthesis via C(15)-(S)-epimers, since this stereochemical change would destabilize the hemiketal that plagued the attempted synthesis of tedanolide via C(15)-(R) intermediates. However, use of C(15)-(S)-configured intermediates required that the side-chain epoxide be introduced very late in the synthesis, owing to the ease with which the C(15)-(S)-OH cyclized onto the epoxide of intermediate 50.
The total synthesis of (+)-tedanolide - A macrocyclic polyketide from marine sponge tedania ignis
Ehrlich, Gunnar,Hassfeld, Jorma,Eggert, Ulrike,Kalesse, Markus
experimental part, p. 2232 - 2247 (2009/04/07)
Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis, is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in bioassays. A unique structural feature of the known tedanolides is the prima
The total synthesis of (+)-tedanolide
Ehrlich, Gunnar,Hassfeld, Jorma,Eggert, Ulrike,Kalesse, Markus
, p. 14038 - 14039 (2007/10/03)
The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations gen
