𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A novel synthesis of the cyclic carbinolamide moiety of the maytansinoids

✍ Scribed by Konstantinos S. Petrakis; Josef Fried

Book ID
104221448
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
132 KB
Volume
24
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The a-diketo urethane 2 cyclizes to form the cyclic carbinolamide 4 using TMS triflate and 2,6-di-t-butylpyridine.

The siloxy group of 3 is readily exchanged in methanol or water to form 5 or 1.

Remarkably, 2 does not cyclize spontaneously or on standard acid catalysis.

πŸ“œ SIMILAR VOLUMES

Studies related to the synthesis of mayt
Studies related to the synthesis of maytansinoids.
✍ Derek H.R. Barton; Michel BΓ©nΓ©chie; FranΓ§oise Khuong-Huu; Pierre Potier; Victor πŸ“‚ Article πŸ“… 1982 πŸ› Elsevier Science 🌐 French βš– 196 KB

Two approaches to the partial synthesis of C1-Cs of a bis-nor maytansinoid 1 have been investigated starting on the one hand with (S)-(-)-malic acid and on the other, with D-(+)-ribonolactone. 2 Maytansinoids are interesting naturally occurringIantitumor agents . 3 Extensive work has already been ca

BUILDING BLOCKS FOR THE SYNTHESIS OF MAY
BUILDING BLOCKS FOR THE SYNTHESIS OF MAYTANSINOIDS
✍ GΓΆtschi, Erwin; Schneider, Fernand; Wagner, Hans; Bernauer, Karl πŸ“‚ Article πŸ“… 1981 πŸ› Taylor and Francis Group 🌐 English βš– 543 KB
A novel diastereoselective synthesis of
A novel diastereoselective synthesis of the lactone moiety of compactin
✍ Kapa Prasad; Oljan Repič πŸ“‚ Article πŸ“… 1984 πŸ› Elsevier Science 🌐 French βš– 186 KB

A new synthesis of racemic $-hydroxy-&lactone 10 with requisite relative stereochemistry as in compactin (la) is described utilizing cis-cyclohexane-1,3,5-trio1 (2) as the starting material. Compactin' (la) and mevinolin\* -(lb) have attracted a great deal of interest from synthetic organic chemists