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Approaches to the synthesis of cytochalasans. Part 8. Further transformations and optical resolution of the tetrahydroisoindolinone subunit

✍ Scribed by Tibur Schmidlin; Daniel Wallach; Christoph Tamm

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

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✦ Synopsis

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, respectively. Treatment of 10 and 11 with Al(i‐PrO)~3~ gave the allylic alcohol 12. Protection of the olefinic double bond was also effected by hydroxylation with OsO~4~. The triol 17 obtained from 3, after acetalization of 18, was oxidized to the aldehyde 20. Attachment of the ylide of the phosphonium salt 1 to 20 gave 24, an intermediate of proxiphomin (2). Removal of the C(6), C(7)‐diol group was achieved via the thiocarbonate 23.

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