𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Approaches to the synthesis of cytochalasans. Part 7. Synthesis of some building blocks for the construction of the macrocyclic moiety

✍ Scribed by Daniel Wallach; Ivan G. Csendes; Peter E. Burckhardt; Tibur Schmidlin; Christoph Tamm

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

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The synthesis of ethyl (2__E__, 4__E__, 8__R__)‐8‐methyl‐10‐[(2__H__‐tetrahydropyran‐2‐yl)oxy]‐2,4‐decadienoate (11), methyl (2__E__, 8__R__)‐8‐methyl‐10‐[(2__H__‐tetrahydropyran‐2‐yl)oxy]‐2‐decenoate (16), synthons for the construction of the macrocyclic moieties of the cytochalasins A, B and F, and of (3__R__)‐[7‐(1,3‐dioxolan‐2‐yl)‐3‐methylheptyl]triphenyl‐phosphonium bromide (24), a C~8~‐building block for deoxaphomin, proxiphomin and protophomin is described. In all instances (+)‐(R)‐pulegone (5) served as starting material.

📜 SIMILAR VOLUMES

Approaches to the Synthesis of Cytochala
Approaches to the Synthesis of Cytochalasans. Part 3. Synthesis of a substituted tetrahydroisoindolinone moiety possessing the same relative configuration as proxiphomin
✍ Tibur Schmidlin; Werner Züurcher; Christoph Tamm 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 769 KB

## Abstract The total synthesis of the tetrahydroisoindolinone moiety corresponding to proxiphomin (**1**) is described, bearing functional groups for the attachment of the macrocyclic ring. __Knoevenagel‐Cope__ condensation of racemic 2‐(benzyloxycarbonyl‐amino)‐3‐phenylpropanal (**2**) with methy

Approaches to the total synthesis of cyt
Approaches to the total synthesis of cytochalasans. A convergent synthesis of the octahydroisoindolone moiety related to proxiphomin. Preliminary communication
✍ Tibur Schmidlin; Christoph Tamm 📂 Article 📅 1978 🏛 John Wiley and Sons 🌐 German ⚖ 218 KB 👁 1 views

## Abstract The octahydroisoindolone moiety related to proxiphomin **(1)** has been synthesized by condensation of __N__‐benzyloxycarbonyl‐protected D, L‐phenylalaninal **(7)** with methyl‐(4‐methyl‐sorbyl)‐malonate **(11)** to yield the branched ethylene derivative **12**. Consecutive intramolecul

Approaches to the Synthesis of Cytochala
Approaches to the Synthesis of Cytochalasans Part9. A versatile concept leading to all structural types of cytochalasans
✍ Jean Ackermann; Michael Matthes; Christoph Tamm 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 German ⚖ 804 KB

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, respe

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 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