𝔖 Bobbio Scriptorium
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Studies related to the synthesis of maytansinoids.

✍ Scribed by Derek H.R. Barton; Michel Bénéchie; Françoise Khuong-Huu; Pierre Potier; Victor Reyna-Pinedo

Book ID
104220413
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
196 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 carried out on the synthesis of maytansine itself . In a projected partial synthesis of the bis-nor-4,6-maytansinoid L(R=H, or ester) in the correct absolute configuration, we have investigated two approaches to the acetylenic acetal 2. This acetal bears at C-3 an hydroxyl group in the correct absolute configuration and by coupling with the epoxide 2 4 would lead, after further manipulation, to the CI-CI1 moiety of 1. After oxidation of the acetal function of 2 to an acid, the amide linkage could, then, been established with the amine function of 4 _' (R, variable).

📜 SIMILAR VOLUMES

Building Blocks for the Synthesis of May
Building Blocks for the Synthesis of Maytansinoids. Preliminary Communication
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## Abstract The dienal **14** and the ketone **19**, both potential building blocks of maytansinoids, were synthesized starting from ethyl vanillate (**2**) __via__ the aldehyde **9**. It could be shown in a preliminary experiment that the dienal **14** can be coupled with 2‐lithio‐1,3‐dithiane to

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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.