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Approaches to the synthesis of cytochalasans. Part 6. Synthesis of the C(14)–C(23) subunit of cytochalasins A, B. F and desoxaphomin

✍ Scribed by Jean Ackermann; Nada Waespe-Šarčevic̀; Christoph Tamm

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
441 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

The synthesis of methyl (4R, 8RJ-lO-bromo-8-methyl-4-( 1,3,6-trioxaheptane)-2-deceneoate (3, a synthon for the construction of the macrocyclic moieties of the cytochalasins A (l), B (2), F (3) and desoxaphomin (4) is described. (S)-Glutamic acid (6) was transformed to the C,-epoxide 10 and 3-methylglutaric acid (11) to the C,-bromide 15. Coupling of both 10 and 15 by a CuI-catalyzed Grignard reaction gave the decanol 16 in very high yield. The latter was transformed by several steps to synthon 5.

The cytochalasans are a family of closely related substances isolated from a variety of moulds and microorganisms. They exhibit a wide range of biological activities which often are used as tools in cell biology [2]. The characteristic structural elements of the cytochalasins A (l), B (2), F( 3) and desoxaphomin (4) are a bicyclic tetrahydroisoindolinone moiety which is fused to an 11-to 14-membered niacrocyclic ring, and its many functional substituents. 0 0 0 0 OH 5 , R=OH , R'=O 1 A6,12 , R=OH , 2 p . 1 2 OH 3 6.7.Epoxy. R=H , R=<' O H 4 ') Part 5: [I].

2, Part of the planed thesis of J . A 1. N a N 0 2 , HCI LiBH,,

📜 SIMILAR VOLUMES

Approaches to the Synthesis of Cytochala
Approaches to the Synthesis of Cytochalasans. Part 4. Improved Synthesis of the Tetrahydroisoindoline Subunits Related to the Cytochalasins and Aspochalasins
✍ Tibur Schmidlin; Peter E. Burckhardt; Nada Waespe-Šarčevic̀; Christoph Tamm 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 851 KB

## Abstract A general scheme for the synthesis of the tetrahydroisoindolinone moiety of naturally occurring cytochalasans and unnatural analogs was developed. The key‐step consists of the __inter__molecular [2+4]cycloaddition of 4‐methylsorbinol (7) to an alkylidene malonic ester derivative such as

Approaches to the synthesis of cytochala
Approaches to the synthesis of cytochalasans. Part 8. Further transformations and optical resolution of the tetrahydroisoindolinone subunit
✍ Tibur Schmidlin; Daniel Wallach; Christoph Tamm 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 German ⚖ 721 KB

## Abstract The bicycle aldehyde **7** was prepared from the hydroxy ester **3** for the attachment of teh macrocyclic moiety of the cytochalasans. To protect the C(6),C(7)‐double bond the intermediates **8**, **9** and **13** were transformed into the epoxides **10**, **11** and **14**, respective