ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 OsO4. 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19840670738