𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Approaches to the Synthesis of Cytochalasans Part9. A versatile concept leading to all structural types of cytochalasans

✍ Scribed by Jean Ackermann; Michael Matthes; Christoph Tamm

Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
804 KB
Volume
73
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Starting from D-glutamic acid (5), the bicyclic compounds 4a and 4b were synthesized via 17 (Schemes 1 and 2). The reaction leading to 4g and 4h with LiCuPhz was not successful. But treatment of the N-protected model lactams 19,21, and 22 with Li,Cu(CN)Ph, gave the amino ketones 24,26, and 27, respectively (Scheme 3). The desired compound 23 was obtained from 20. Conversion of the unprotected lactams 28,31, and 32 gave the phenyl derivative 34 in excellent yields. Ester 35 was transformed to the a -amino-y-0x0-acid derivative 36. This conversion opens a novel access to this type of compounds.

📜 SIMILAR VOLUMES

Approaches to the Synthesis of Cytochala
Approaches to the Synthesis of Cytochalasans. Part 2. Pyrrolinone derivatives as basic units
✍ Tibur Schmidlin; Christoph Tamm 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 632 KB

## Abstract Several attempts to prepare 3‐acetyl‐5‐benzyl‐3‐pyrrolin‐2‐one (**7**) from phenylalanine are described. This goal was only reached formally, because compound **7** exists in the tautomeric form of (Z)‐5‐benzyl‐3‐(1′‐hydroxyethylidene)‐4‐pyrrolin‐2‐one (**17**) according to the spectral

Approaches to the synthesis of cytochala
Approaches to the synthesis of cytochalasans. Part 5. Studies on the selectivity of the Diels-Alder reaction leading to the tetrahydroiso-indolinone sub-unit
✍ Tibur Schmidlin; Remo Gamboni; Peter Strazewski; Christoph Tamm 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 619 KB

## Abstract The stereo‐ and regiochemical course in the [2+4]cycloaddition of the chiral alkylidene malonic ester **1** to selected derivatives of (2__E__, 4__E__)‐4‐methyl‐2, 4‐hexadien‐l‐ol (**2**) and (2__E__, 4__E__)‐4‐methyl‐2, 4‐hexadien‐l‐al (**12**) has been investigated. The results are di

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

Approaches to the Synthesis of Cytochala
Approaches to the Synthesis of Cytochalasans. Part 11. Further transformations and cyclization attempts directed towards proxiphomin
✍ Markus Boutellier; Daniel Wallach; Christoph Tamm 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 German ⚖ 852 KB

## Abstract Starting from iodoalcohol 9, the monoprotected dialdehyde 5 was synthesized (__Scheme 2__) and converted to 17 by reaction with oxo‐phosphonate 15 (__Scheme 3__). The latter was prepared from 13. Cyclisation of 17 to the target compound 18 failed. Also the attachment of thiol 22 to lact