Short synthesis of the 6,6-spiroketal cores of spirofungins A and B.
[reaction: see text] Initial efforts toward the total synthesis of the antifungal antibiotics spirofungins A and B are reported. A short and efficient synthesis of the C9-C20 6,6-spiroketal fragments of both compounds is described. This asymmetric approach uses a very efficient alkylation of a lithiated N,N-dimethylhydrazone followed by spiroketal formation under acidic conditions.
Dias
Luiz C
LC
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154 13084-971, Campinas, SP, Brazil. ldias@iqm.unicap.br
de Oliveira
Luciana G
LG
D000478:Alkylation; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*
D000935:Antifungal Agents; D011714:Pyrans; D013141:Spiro Compounds; C114877:spirofungin A; C493365:spirofungin B