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Approaches to the Synthesis of Cytochalasans. Part 4. Improved Synthesis of the Tetrahydroisoindoline Subunits Related to the Cytochalasins and Aspochalasins

✍ Scribed by Tibur Schmidlin; Peter E. Burckhardt; Nada Waespe-Šarčevic̀; Christoph Tamm

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
851 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 6, 9 or 10, obtained from the corresponding amino acids. The products obtained, 4a, 17, and 18 were converted to the desired lactams 5, 21, and 22.

Cycloaddition of the diene alcohol 7 to the optically active alkylidene malonic ester derivative 9b (s. Footnote 5) prepared from L‐leucine gave compound 17b with 98% enantiomeric excess. The optical activity was retained during the conversion of 17b to the lactam 21b. The latter is a subunit for the synthesis of the aspochalasins.

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