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Spiroketal equilibration: Interconversion of 1,6-dioxaspiro[4.4]nonanes and 1,6-dioxaspiro[4.5]decanes. Implications for the synthesis of cephalostatin 7

✍ Scribed by Jae Uk Jeong; P.L. Fuchs

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 279 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73506-4

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✦ Synopsis

Acid-catalyzed equilibration of spiroketals 5SHp6 and 55Haj3 involves a two stage process whereby the 1,6-dioxaspiro]4.4]nonanes can be equilibrated under mild conditions to a pair of 1,6_dioxaspiro[45]decanes with preservation of the adjacent C-20 methyl stereocenter. Under more forcing conditions, both centers can be equilibrated in a reaction involving vinyl ether intermediate 10H. Cephalostatin 7 3 is a potent member of a family of eleven trisdecacyclic pyrazines characterized by Pettit.2 These materials are also highly active (10-g-10-10 M) in a

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